Multi-step reaction with 22 steps
1.1: (+)-diisopropyl tartrate; titanium isopropoxide; tert-butyl hydroperoxide / CH2Cl2; decane / -20 °C
2.1: 95 percent / pyridine / CH2Cl2 / 48 h / -10 °C
3.1: perchloric acid / tetrahydrofuran; H2O / 2 h / Heating
3.2: 67 percent / 2,6-lutidine / CH2Cl2 / 1 h / -20 °C
4.1: vanadil acetylacetonate; t-butyl hydroperoxide; pyridinium para-toluenesulfonate / 4 Angstroem molecular sieve / various solvent(s); CH2Cl2; decane / 29 h / 20 °C
5.1: sodium iodide; 18-c-6 / butan-2-one / Heating
5.2: 81 percent / tributyltin hydride; AIBN / toluene / 3 h / Heating
6.1: 93 percent / triethylamine / CH2Cl2 / 3 h / -78 °C
7.1: n-butyl lithium / tetrahydrofuran; hexane / 0.5 h / -78 °C
7.2: tetrahydrofuran; hexane / 0.5 h
8.1: N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH2Cl2 / 2 h / 20 °C
9.1: 673 mg / samarium diiodide / ethanol; tetrahydrofuran / 0.5 h / -78 °C
10.1: 86 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H2O; CH2Cl2 / 1 h / 0 °C
11.1: 90 percent / samarium diiodide / tetrahydrofuran / 0.5 h / 0 °C
12.1: 4-dimethylaminopyridine / CH2Cl2
13.1: HCl / tetrahydrofuran / 5 h / 0 °C
14.1: 264 mg / sodium hydride / tetrahydrofuran / 0.33 h / 50 °C
15.1: 96 percent / Pd(OH)2 / ethanol; cyclohexane / 12 h / Heating
16.1: 91 percent / N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH2Cl2 / 0.5 h / 20 °C
17.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h
17.2: 85 percent / tetrahydrofuran; toluene / -78 - 20 °C
18.1: 97 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H2O; CH2Cl2 / 2 h / 0 °C
19.1: DMSO; oxalyl chloride; Et3N / CH2Cl2 / 0.92 h / -78 °C
20.1: dibutylboron triflate; diisopropylethylamine / CH2Cl2 / 0.5 h / -78 °C
20.2: CH2Cl2 / 3 h / -78 - 20 °C
21.1: 12 mg / pyridine; chromium trioxide / CH2Cl2 / 0.33 h / 20 °C
22.1: 85 percent / HF / H2O; acetonitrile / 3 h / 20 °C
With
pyridine; chromium(VI) oxide; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; n-butyllithium; perchloric acid; samarium diiodide; oxalyl dichloride; bis(acetylacetonate)oxovanadium; L-(+)-diisopropyl tartrate; 18-crown-6 ether; di-n-butylboryl trifluoromethanesulfonate; hydrogen fluoride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide;
palladium dihydroxide; tetrapropylammonium perruthennate; 4 A molecular sieve;
In
tetrahydrofuran; decane; ethanol; hexane; dichloromethane; cyclohexane; water; toluene; acetonitrile; butanone;
11.1: Tishchenko reaction / 17.1: Julia reaction / 19.1: Swern oxidation / 21.1: Collins oxidation;
DOI:10.1021/ol025872f