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通过串联异构化-脱乙酰化-环化异构化，从 MBH-乙酰乙酸酯合成取代的 3-呋喃酯：通向 Elliott 醇。

Synthesis of substituted 3-furanoates from MBH-acetates of acetylenic aldehydes via tandem isomerization-deacetylation-cycloisomerization: access to Elliott's alcohol.

机构信息

Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad - 500607, India.

出版信息

Org Biomol Chem. 2014 Mar 14;12(10):1664-70. doi: 10.1039/c3ob42396d.

DOI:10.1039/c3ob42396d
PMID:24492976
Abstract

A new method for the synthesis of 5-substituted furan-3-carboxylates from Morita-Baylis-Hillman acetates of acetylenic aldehydes is reported. The process involves palladium-catalyzed isomerization followed by base-promoted deacetylation and cycloisomerization reactions. The utility of this chemistry is further demonstrated by the synthesis of Elliott's alcohol, a key intermediate of the pyrethroid resmethrins.

摘要

报道了一种从炔基醛的 Morita-Baylis-Hillman 乙酸酯合成 5-取代呋喃-3-羧酸酯的新方法。该过程涉及钯催化的异构化，然后是碱促进的脱乙酰化和环化异构化反应。该化学的实用性进一步通过合成 Elliott 醇得到证明，Elliott 醇是拟除虫菊酯 resmethrins 的关键中间体。

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