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198481-99-1
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Basic Information
CAS No.: 198481-99-1
Name: Salicylihalamide A
Article Data: 8
Molecular Structure:
Molecular Structure of 198481-99-1 (Salicylihalamide A)
Formula: C26H33NO5
Molecular Weight: 439.552
Synonyms: salicylhalamide A;salicylihalamide A;(2Z,4Z)-Hepta-2,4-dienoic acid [(E)-3-((E)-(7S,9R,10S)-4,9-dihydroxy-10-methyl-5-oxo-7,8,9,10,11,14-hexahydro-5H-6-oxa-benzocyclododecen-7-yl)-propenyl]-amide;
Density: 1.111g/cm3
Boiling Point: 708.3°Cat760mmHg
Flash Point: 382.2°C
PSA: 95.86000
LogP: 4.74040
Related products
Synthetic route
350794-14-8

bis[teri-butyl(dimethyl)silyl]-salicylihalamide

198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
With pyridine hydrogenfluoride In tetrahydrofuran; pyridine for 72h;78%
With pyridine hydrogenfluoride In tetrahydrofuran at 23℃; for 72h;75%
325172-28-9

2-allyl-6-methoxy-benzoic acid

198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1: 84 percent / triphenylphosphine; diethyl azodicarboxylate / benzene / 24 h
2: (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 0.67 h / 20 °C
3: 98 percent / DDQ; buffer / CH2Cl2; H2O / 0.75 h / 20 °C / pH 7
4: 98 percent / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
5: 82 percent / BBr3 / CH2Cl2 / 3 h / -78 °C
6: 97 percent / sodium chlorite; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 1 h
7: triethylamine / CH2Cl2 / 2 h / 20 °C
8: 21 mg / K2CO3; H2O / methanol; tetrahydrofuran / 0.08 h / 20 °C
9: N,N-diisopropylethylamine / acetone / 0 - 20 °C
10: sodium azide / acetone; H2O / 0.5 h / 20 °C
11: toluene / 0.25 h / 110 °C
12: 21.6 mg / toluene / 0.17 h / Heating
13: 81 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran; benzene / 0.17 h / 0 °C
14: tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C
15: 2.6 mg / HF*py / tetrahydrofuran; pyridine / 48 h / 20 °C
View Scheme
Multi-step reaction with 12 steps
1.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
2.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
3.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
4.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
5.1: NaH / tetrahydrofuran / 1 h / 0 °C
6.1: 64 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
7.1: Ba(OH)2*8H2O / tetrahydrofuran / 20 °C
8.1: imidazole; DMAP / dimethylformamide / 20 °C
9.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
10.1: benzene / 6 h / 75 °C
11.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
11.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
12.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 12 steps
1.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
2.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
3.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
4.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
5.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C
6.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
7.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
8.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
9.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
10.1: benzene / 6 h / 75 °C
11.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
11.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
12.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 9 steps
1: DEAD; PPh3 / diethyl ether / 1 h / 0 - 20 °C
2: bis(tricyclohexylphosphine)benzylidine ruthenium(VI) Cl2 / CH2Cl2 / 3 h / Heating
3: BBr3 / CH2Cl2 / 0.5 h / -78 °C
4: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 0.5 h / 20 °C
5: DIPEA; DMAP / dimethylformamide / 1 h / 70 °C
6: TMSOTf / 1,2-dichloro-ethane / 2 h / 20 °C
7: NaH / various solvent(s) / 4.5 h / 60 °C
8: TBAF / tetrahydrofuran / 1 h / 20 °C
9: TBAF; HMPA / tetrahydrofuran / 48 h / 40 °C
View Scheme
Multi-step reaction with 9 steps
1: DEAD; PPh3 / diethyl ether / 1 h / 0 - 20 °C
2: bis(tricyclohexylphosphine)benzylidine ruthenium(VI) Cl2 / CH2Cl2 / 3 h / Heating
3: BBr3 / CH2Cl2 / 0.5 h / -78 °C
4: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 0.5 h / 20 °C
5: DIPEA; DMAP / dimethylformamide / 1 h / 70 °C
6: TMSOTf / 1,2-dichloro-ethane / 2 h / 20 °C
7: NaH / various solvent(s) / 4.5 h / 60 °C
8: TBAF / tetrahydrofuran / 1 h / 20 °C
9: TBAF; HMPA / tetrahydrofuran / 48 h / 40 °C
View Scheme
398478-59-6

(7S,9R,10S,12E)-(4-methoxy-9-methoxymethoxy-10-methyl-5-oxo-7,8,9,10,11,14-hexahydro[5H]-6-oxa-benzocyclododecen-7-yl)-acetaldehyde

198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: NaH / tetrahydrofuran / 1 h / 0 °C
2.1: 64 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
3.1: Ba(OH)2*8H2O / tetrahydrofuran / 20 °C
4.1: imidazole; DMAP / dimethylformamide / 20 °C
5.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
6.1: benzene / 6 h / 75 °C
7.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
7.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
8.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C
2.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
3.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
4.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
5.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
6.1: benzene / 6 h / 75 °C
7.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
7.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
8.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 87 percent / CrCl2 / tetrahydrofuran; dioxane / 16 h / 20 °C
2: 88 percent / BBr3 / CH2Cl2 / 1 h / -78 °C
3: copper(I) thiophene-2-carboxylate; Rb2CO3 / N,N-dimethyl-acetamide / 2 h / 90 °C
View Scheme
Multi-step reaction with 7 steps
1.1: NaH / tetrahydrofuran / 0 °C
2.1: 92 percent / BBr3 / CH2Cl2 / -78 °C
3.1: 95 percent / imidazole / dimethylformamide
4.1: 97 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran
5.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
6.1: benzene / 6 h / 75 °C
7.1: t-BuLi / diethyl ether; tetrahydrofuran / 0.75 h / -78 °C
7.2: diethyl ether; tetrahydrofuran / -78 - 0 °C
7.3: HF*pyridine / pyridine; tetrahydrofuran / 48 h / 20 °C
View Scheme
320573-55-5

(12E)-(7S,9R,10S)-7-(2-hydroxyethyl)-4-methoxy-9-methoxymethoxy-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclodecen-5-one

198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
2.1: NaH / tetrahydrofuran / 1 h / 0 °C
3.1: 64 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
4.1: Ba(OH)2*8H2O / tetrahydrofuran / 20 °C
5.1: imidazole; DMAP / dimethylformamide / 20 °C
6.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
7.1: benzene / 6 h / 75 °C
8.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
8.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
9.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 9 steps
1.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
2.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C
3.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
4.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
5.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
6.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
7.1: benzene / 6 h / 75 °C
8.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
8.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
9.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: 87 percent / Dess-Martin periodinane / CH2Cl2 / 18 h / 20 °C
2: 87 percent / CrCl2 / tetrahydrofuran; dioxane / 16 h / 20 °C
3: 88 percent / BBr3 / CH2Cl2 / 1 h / -78 °C
4: copper(I) thiophene-2-carboxylate; Rb2CO3 / N,N-dimethyl-acetamide / 2 h / 90 °C
View Scheme
Multi-step reaction with 8 steps
1.1: Dess-Martin periodinane / CH2Cl2
2.1: NaH / tetrahydrofuran / 0 °C
3.1: 92 percent / BBr3 / CH2Cl2 / -78 °C
4.1: 95 percent / imidazole / dimethylformamide
5.1: 97 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran
6.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
7.1: benzene / 6 h / 75 °C
8.1: t-BuLi / diethyl ether; tetrahydrofuran / 0.75 h / -78 °C
8.2: diethyl ether; tetrahydrofuran / -78 - 0 °C
8.3: HF*pyridine / pyridine; tetrahydrofuran / 48 h / 20 °C
View Scheme
398478-58-5

(3S,5R,6S,E)-14-methoxy-3-(2-((4-methoxybenzyl)oxy)-ethyl)-5-(methoxymethoxy)-6-methyl-3,4,5,6,7,10-hexahydro-1H-benzo[c][1]oxacyclododecin-1-one

198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
2.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
3.1: NaH / tetrahydrofuran / 1 h / 0 °C
4.1: 64 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
5.1: Ba(OH)2*8H2O / tetrahydrofuran / 20 °C
6.1: imidazole; DMAP / dimethylformamide / 20 °C
7.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
8.1: benzene / 6 h / 75 °C
9.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
9.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
10.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 10 steps
1.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
2.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
3.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C
4.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
5.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
6.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
7.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
8.1: benzene / 6 h / 75 °C
9.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
9.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
10.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: 94 percent / DDQ / H2O; CH2Cl2 / 12 h / 20 °C
2: 87 percent / Dess-Martin periodinane / CH2Cl2 / 18 h / 20 °C
3: 87 percent / CrCl2 / tetrahydrofuran; dioxane / 16 h / 20 °C
4: 88 percent / BBr3 / CH2Cl2 / 1 h / -78 °C
5: copper(I) thiophene-2-carboxylate; Rb2CO3 / N,N-dimethyl-acetamide / 2 h / 90 °C
View Scheme
320573-58-8

(12E)-(7S,9R,10S)-7-[(2E)-3-(carboallyloxy)prop-2-enyl]-4,9-dihydroxy-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclodecen-5-one

198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
2.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
3.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
4.1: benzene / 6 h / 75 °C
5.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
5.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
6.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: 95 percent / imidazole / dimethylformamide
2.1: 97 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran
3.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
4.1: benzene / 6 h / 75 °C
5.1: t-BuLi / diethyl ether; tetrahydrofuran / 0.75 h / -78 °C
5.2: diethyl ether; tetrahydrofuran / -78 - 0 °C
5.3: HF*pyridine / pyridine; tetrahydrofuran / 48 h / 20 °C
View Scheme
320573-59-9

(12E)-(7S,9R,10S)-4,9-bis-(tert-butyldimethylsilyloxy)-7-[(2E)-3-(carboallyloxy)prop-2-enyl]-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclodecen-5-one

198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
2.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
3.1: benzene / 6 h / 75 °C
4.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
4.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
5.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: 97 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran
2.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
3.1: benzene / 6 h / 75 °C
4.1: t-BuLi / diethyl ether; tetrahydrofuran / 0.75 h / -78 °C
4.2: diethyl ether; tetrahydrofuran / -78 - 0 °C
4.3: HF*pyridine / pyridine; tetrahydrofuran / 48 h / 20 °C
View Scheme
164014-40-8

2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)benzodioxin-4-one

Me2CuLi

Me2CuLi

198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 16 steps
1.1: 1.3 g / LiCl; Pd2(dba)3; tri-(2-furyl)phosphine / 1-methyl-pyrrolidin-2-one / 48 h / 20 °C
2.1: EtMgBr / tetrahydrofuran / 0.25 h / 20 °C
2.2: 90 percent / tetrahydrofuran / 7.5 h / 20 - 60 °C
3.1: 98 percent / K2CO3 / acetone / 40 h / 20 °C
4.1: 96 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 1 h / 20 °C
5.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
6.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
7.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
8.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
9.1: NaH / tetrahydrofuran / 1 h / 0 °C
10.1: 64 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
11.1: Ba(OH)2*8H2O / tetrahydrofuran / 20 °C
12.1: imidazole; DMAP / dimethylformamide / 20 °C
13.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
14.1: benzene / 6 h / 75 °C
15.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
15.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
16.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 16 steps
1.1: 1.3 g / LiCl; Pd2(dba)3; tri-(2-furyl)phosphine / 1-methyl-pyrrolidin-2-one / 48 h / 20 °C
2.1: EtMgBr / tetrahydrofuran / 0.25 h / 20 °C
2.2: 90 percent / tetrahydrofuran / 7.5 h / 20 - 60 °C
3.1: 98 percent / K2CO3 / acetone / 40 h / 20 °C
4.1: 96 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 1 h / 20 °C
5.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
6.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
7.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
8.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
9.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C
10.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
11.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
12.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
13.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
14.1: benzene / 6 h / 75 °C
15.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
15.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
16.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
204846-40-2

2,2-dimethyl-5-(2-propenyl)-4H-1,3-benzodioxin-4-one

198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1.1: EtMgBr / tetrahydrofuran / 0.25 h / 20 °C
1.2: 90 percent / tetrahydrofuran / 7.5 h / 20 - 60 °C
2.1: 98 percent / K2CO3 / acetone / 40 h / 20 °C
3.1: 96 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 1 h / 20 °C
4.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
5.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
6.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
7.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
8.1: NaH / tetrahydrofuran / 1 h / 0 °C
9.1: 64 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
10.1: Ba(OH)2*8H2O / tetrahydrofuran / 20 °C
11.1: imidazole; DMAP / dimethylformamide / 20 °C
12.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
13.1: benzene / 6 h / 75 °C
14.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
14.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
15.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 15 steps
1.1: EtMgBr / tetrahydrofuran / 0.25 h / 20 °C
1.2: 90 percent / tetrahydrofuran / 7.5 h / 20 - 60 °C
2.1: 98 percent / K2CO3 / acetone / 40 h / 20 °C
3.1: 96 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 1 h / 20 °C
4.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
5.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
6.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
7.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
8.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C
9.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
10.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
11.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
12.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
13.1: benzene / 6 h / 75 °C
14.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
14.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
15.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
325172-48-3

2-methoxy-6-(prop-2-enyl)benzoic acid allyl ester

198481-99-1

(-)-salicylihalamide A

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: 96 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 1 h / 20 °C
2.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
3.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
4.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
5.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
6.1: NaH / tetrahydrofuran / 1 h / 0 °C
7.1: 64 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
8.1: Ba(OH)2*8H2O / tetrahydrofuran / 20 °C
9.1: imidazole; DMAP / dimethylformamide / 20 °C
10.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
11.1: benzene / 6 h / 75 °C
12.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
12.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
13.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 13 steps
1.1: 96 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 1 h / 20 °C
2.1: 88 percent / DEAD; PPh3 / diethyl ether / 4 h / Heating
3.1: 8 percent / Cl2[(Cy)3P]2Ru=CHPh / CH2Cl2 / 4 h / 20 °C
4.1: 96 percent / DDQ; H2O / CH2Cl2 / 1.5 h / 20 °C
5.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C
6.1: 93 percent / NaH / tetrahydrofuran / 1 h / 0 °C
7.1: 81 percent / BBr3 / CH2Cl2 / 0.33 h / -78 °C
8.1: 92 percent / imidazole; DMAP / dimethylformamide / 10 h / 20 °C
9.1: 96 percent / morpholine / Pd(PPh3)4 / tetrahydrofuran / 4 h / 20 °C
10.1: 92 percent / (PhO)2P(O)N3; Et3N / benzene / 14 h / 20 °C
11.1: benzene / 6 h / 75 °C
12.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C
12.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
13.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
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