Ring Expansion of Cyclic α-Ethynyl Sulfonium Ylides by [2,3]-Sigmatropic Rearrangement : Formation of Thiocin, Thionin, and Thiecin Derivatives

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概要

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• The cyclic 1-ethoxycarbonylmethyl-2-ethynyl sulfonium salts (15Aa-d, 15Ba-d, and 15Ca-d), prepared from thiolane (12A), thiane (12B), and thiepane (12C), were treated with 1,5-diazabicyclo[5.4.0]undec-5-ene (DBU) to result in ring expansion, giving thiocins (18Aa-d), thionins (18Ba-d), and thiecins (18Ca-d), respectively, presumably via the allenic intermediates (17) derived from the initially formed sulfonium ylides (16) by [2,3]-sigmatropic rearrangement. Similarly, the 1- (27a-c) and 3-benzothionins (30a-c) were obtained from 2-ethynylthiochromans (21) and 1-ethynylisothiochromans (22), respectively, via the sulfonium ylides (25,28) and the allenic compounds (26,29) successively.

• 公益社団法人日本薬学会の論文
• 1986-09-25

著者

• 土屋 隆

  Faculty of Pharmaceutical Sciences, Hokuriku University

• 土屋 隆

  School of Pharmacy, Hokuriku University

• 指田 春喜

  School of Pharmacy, Hokuriku University

• 指田 春喜

  北陸大学薬学部

• 指田 春喜

  Faculty Of Pharmaceutical Sciences Hokuriku University

• 土屋 隆

  Faculty Of Pharmaceutical Sciences Hokuriku University

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