1 0 0 0 OA Preparation of Optically Active γ-Hydroxyethyl α, β-Unsaturated γ-Lactone Using an Enzymatic
- 著者
- 末宗 洋 肥塚 美千代 鎌下 知子 酒井 浄
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.37, no.5, pp.1379-1381, 1989-05-25 (Released:2008-03-31)
- 参考文献数
- 8
- 被引用文献数
- 15 21
γ-Hydroxyethyl α, β-unsaturated γ-lactone (2) is a promising intermediate for the synthesis of eldanolide and cis, cis-1, 2, 3-trisubstituted cyclopentane, which could be converted to 11-deoxyprostaglandins. In order to prepare optically active 2, enzymatic hydrolysis of (±)-trans-cyclohexene-4, 5-diacetate with Pseudomonas fluorescens lipase was examined, and the monoalcohol ((-)-6, >99%ee)with R-configuration was obtained in accored with prediction based on the three-site model proposed by us. Compound (-)-6 could be converted to the chiral lactone ((-)-2) via a sequence of reactions involving ring cleavage.
- 著者
- 肥塚 美千代 方 成林 末宗 洋 酒井 浄
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.37, no.5, pp.1185-1187, 1989-05-25 (Released:2008-03-31)
- 参考文献数
- 8
- 被引用文献数
- 9 12
1, 4-Addition of organocopper reagents to γ-substituted α, β-unsaturated γ-lactones followed by intramolecular trapping of the resulted enolates afforded cis, cis-1, 2, 3-trisubstituted cyclopentanes and cyclohexanes in a stereocontrolled manner. This new cyclization reaction to cyclopentanes provides a new synthetic route to the key intermediate in the synthesis of 11-deoxyprostaglandins.
- 著者
- 肥塚 美千代 林 教行 鎌下 知子 末宗 洋 酒井 浄
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.36, no.4, pp.1550-1553, 1988-04-25 (Released:2008-03-31)
- 参考文献数
- 10
- 被引用文献数
- 13 14
2, 6-Dioxabicyclo[3.3.0]octan-3, 7-dione seems to be a promising compound for the synthesis of natural products such as epoxyeicosatrienoic acid, laurediol, and eldanolide. This compound, consisting of two γ-lactones, could be prepared by double lactonization of the silver salt of trans-3-hexenedioic acid using iodine. Starting with this bis-lactone, (±)-eldanoide could by synthesized in a stereocontrolled manner.