天然有機化合物討論会講演要旨集
Online ISSN : 2433-1856
セッションID: 24
会議情報
24 2-Deoxycrustecdysoneの全合成
亀谷 哲治津吹 政可日暮 勝之加藤 正本多 利雄
著者情報
会議録・要旨集 フリー

詳細
抄録

The stereocontrolled synthesis of steroid side chain has been developed. The major interest has been forcused on the synthesis of the side chain of ecdysone as well as crustecdysone from 20-oxosteroid via furan derivatives. Reduction of the olefin (21) over palladium-carbon afforded the (20S)-20-furylsteroid (22), stereoselectively, whose hydrogenation over rhodium-alumina, followed by ruthenium tetroxide oxidation and treatment with methylmagnesium bromide, gave the triols (28) and (29) having an ecdysone-type side chain, respectively. The stereoselective reduction of the lactone (33) as a key reaction to give the δ-lactone (35) and the γ-lactone (36), under various conditions has also been investigated. Grignard reaction of both lactones with methylmagnesium bromide led to the synthesis of the tetraol (37) possessing a crustecdysone side chain. The total synthesis of 2-deoxycrustecdysone (3) has also been achieved by application of the above method.

著者関連情報
© 1985 天然有機化合物討論会電子化委員会
前の記事 次の記事
feedback
Top