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: 18
会議情報
18 中・大員環化合物における立体化学制御 : ゲルマクラン骨格の構築およびペリプラノン-Bの全合成
高橋 孝志根本 尚夫神田 裕辻 二郎藤瀬 裕深沢 義正三浦 巌
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会議録・要旨集 フリー

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A novel construction method for germacrene skeleton such as 3,7-dimethyl-10S^*-(1-methylethenyl)-2E,6E-cyclodecadien-1S^*-ol (18) by the stereoselective [2,3]-Wittig rearrangement of 3,6,10-trimethyl -1-oxa-2E,5E,9E-cyclotridecatriene (15) is presented. The stereoselectivity of this [2,3]-Wittig rearrangement is discussed based on the MM2 calculation. The stereoselective synthesis of(±) -4S^*-isopropyl-7R^*-(t-butyldiphenylsiloxy)methyl-9R^*,10R^*-epoxy-5-cyclodecen-1-one (43), as a precursor of Periplanone-B; the potent sex attractant and sex exitant pheromone of the American cockroach, is presented. In this synthesis,the 10-membered ring is constructed by the intramolecular alkylation of carbanion, generated from the protected cyanohydrin 41 and the stereoselective epoxydation of the enone 31 provides only the desired isomer 43. The stereoselectivity of the epoxydation is also discussed based on the MM2 calculation.

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© 1985 天然有機化合物討論会電子化委員会
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