- Electochemical asymmetric dimerization of cinnamic acid derivatives and application to the enantioselective syntheses of furofuran lignans
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A new electrochemical method for the asymmetric oxidative dimerization of cinnamic acid derivatives has been developed. This method enabled the enantioselective syntheses of furofuran lignans, yangambin, sesamin and eudesmin.
- Mori, Naoki,Furuta, Akiko,Watanabe, Hidenori
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p. 8393 - 8399
(2016/12/06)
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- Simple and efficient asymmetric synthesis of furofuran lignans yangambin and caruilignan A
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A novel asymmetric dimerization of cinnamic acid derivative was achieved in high efficiency and high stereoselectivity. By using the reaction as a key step, two furofuran lignans, yangambin and caruilignan A were synthesized in optically pure form in only 5 and 6 steps, respectively. Georg Thieme Verlag Stuttgart.
- Mori, Naoki,Watanabe, Hidenori,Kitahara, Takeshi
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p. 400 - 404
(2007/10/03)
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- Stereoselective total synthesis of furofuran lignans through dianion aldol condensation
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Highly stereoselective total synthesis of (+)-eudesmin, (+)-yangambin, (-)-eudesmin, and (-)-yangambin is described. This method is useful to generate the core skeleton of furofuran rings utilizing modification of Evans asymmetric aldol condensation.
- Jung, Jae-Chul,Kim, Ju-Cheun,Moon, Hyung-In,Park, Oee-Sook
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p. 6433 - 6437
(2007/10/03)
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- Photoinduced molecular transformations. 157. A new stereo- and regioselective synthesis of 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane lignans involving a β-scission of alkoxyl radicals as the key step. New total syntheses of (±)-sesamin, (±)-eudesmin, and (±)-yangambin
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New total syntheses of naturally occurring 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane lignans, (±)-sesamin and (±)-eudesmin, and the first total synthesis of (±)-yangambin were achieved according to a general method devised by Suginome and colleagues for replacing the carbonyl group of the cyclopentanone ring with an oxygen atom to give a corresponding tetrahydrofuran ring involving a regioselective β-scission of alkoxyl radicals; arylation of dimethyl, diallyl, or dibenzyl 3,7-dioxobicyclo[3.3.0]octane-2,6-dicarbonate (18 and 19a,b) with aryllead triacetate 9a-c, followed by dealkoxycarbonylation of the resulting arylated product 20a-f, gave 2,6-diaryl-3,7-dioxobicyclo[3.3.0]octane 21a-c. A regioselective Baeyer-Villiger oxidation of 21a-c with m-CPBA-NaHCO3 or -K2CO3 gave the corresponding δ-lactone 22a-c, which was reduced with DIBAL to give the corresponding lactol 23a-c. The irradiation of a solution of the hypoiodite of 23a-c, generated in situ with mercury(II) oxide-iodine, in benzene with Pyrex-filtered light resulted in a regioselective β-scission of the corresponding alkoxyl radical to give iodo formate 24a-c. Heating 24a-c in MeOH with NaBH4 gave (±)-sesamin (25a), (±)-eudesmin (25b), or (±)-yangambin (25c).
- Suginome,Orito,Yorita,Ishikawa,Shimoyama,Sasaki
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p. 3052 - 3064
(2007/10/02)
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