A Concise Total Synthesis of (±)-3-Demethoxyerythratidinone Based on an Acid-Promoted Double Cyclization of α-Sulfinylacetamides

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概要

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• The total synthesis of the Erythrina alkaloid (±)-3-demethoxyerythratidinone (20) has been accomplished in 39% overall yield from homoveratrylamine(1)by 8 chemical operations, using a tandem cationic cyclization of the Pummerer rearrangement intermediate derived from the sulfoxide 5 as the key step. Of particular interest is the observation that heating of 5 with p-toluenesulfonic acid provides the erythrinan 6 (and the deprotected derivative 7) as a single stereoisomer, whereas similar treatment of 5 in the presence of ethylene glycol gives initially the bicyclic lactam 8,which then cyclizes under the reaction conditions used to afford a mixture of two diastereomeric erythrinans 6 and 9.A possible explanation of these contrasting results is presented.

• 社団法人日本薬学会の論文
• 1990-04-25

著者

• 池田 正澄

  Kyoto Pharmaceutical University

• 池田 正澄

  京都薬科大学

• 石橋 弘行

  Kyoto Pharmaceutical University

• 石川 こずえ

  Kyoto Pharmaceutical University

• 石橋 弘行

  金沢大学薬学部

• 石橋 弘行

  京都薬科大学

• 佐藤 達典

  京都薬科大学

• 佐藤 達典

  Kyoto Pharmaceutical University

• 高橋 雅子

  Kyoto Pharmaceutical University

• 林 真由美

  Kyoto Pharmaceutical University

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