An Useful Synthetic Method for 3-Substituted .DELTA.-Lactones. Synthesis of (.+-.)-Secocrispiolide.

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概要

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• 2-Phenylthio-2-penten-5-olide (<B>1</B>) acted as a reactive Michael acceptor toward some typical carbon neucleophiles to give 3-substituted 2-phenylthio-5-pentanolides (<B>2</B>) which were convertible both to 3-substituted 5-pentanolides by reductive desulfurization and to 3-substituted 2-penten-5-olides by sulfenic acid <I>syn</I> elimination of the sulfoxides <B>4</B> derived from <B>2</B>. The Pummerer rearrangement of <B>4</B> provided 3-substituted 2-phenylthio-2-penten-5-olides and/or 2-hydroxy-2-penten-5-olides. (±)-Secocrispiolide was synthesized via the adduct obtained by the Michael reaction of <B>1</B> with the Grignard reagent prepared from 2,6-dimethylbenzyl bromide and magnesium.

• 公益社団法人 日本化学会の論文

著者

• Yoshikoshi Akira

  Chemical Research Institute Of Non-aqueous Solutions Tohoku University

• Kato Michiharu

  Chemical Research Institute of Non-Aqueous Solutions, Tohoku University

• Ouchi Akihiko

  Chemical Research Institute of Non-Aqueous Solutions, Tohoku University

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