Synthesis of Bridged Steroids. VII. B-Norsteroids having a Gibbane B-C-D Ring System. (2). Synthesis of the 7-Deoxygibberellin Type Ring System

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概要

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• Synthesis of 3a-methylene-3β, 5β-ethano-B-nor-5β-androstane 6β-carboxylic acid (1) having a gibbane B-C-D ring system is described. 5β-Cyano-6β-vinyl-B-nor-5β-androstan-3-one (5), the starting material, was transfomed stereoselectively to 3α-tosyloxy-5β-(trans-β-formyl) vinyl-6β-vinyl-5β-androstane (22d), the key intermediate, by the eight-step synthesis. The latter, after selective ozonization was subjected to a new cyclization method involving participation of 6β-hemiacetal function to afford 3β, 5β-etheno derivative (38), which on subsequent oxidation and the Wolff-Kishner reduction, led to the desired compound (1). Some attempted experiments for homologation at the 5β-nitrile function are also described.

• 社団法人日本薬学会の論文
• 1971-08-25

著者

• 早瀬 善男

  Shionogi Research Laboratory, Shionogi & Co., Ltd.

• 山口 正明

  Shionogi Research Laboratory Shionogi & Co. Ltd.

• 永田 亘

  塩野義製薬株式会社研究所

• 成定 昌幸

  塩野義製薬株式会社研究所

• 早瀬 善男

  Shionogi Research Laboratory Shionogi & Co. Ltd.

• 若林 利生

  Shionogi Research Laboratory:(present Address)central Research Institute Teijin Limited

• 早瀬 善男

  Shionogi And Co. Ltd. Shiga Jpn

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