An improved synthetic method for dL-griseofulvin and its 2-S-analogue

Masatoshi Yamato; Yasuo Takeuchi; Hideo Tomozane

doi:10.1055/s-1990-26942

An improved synthetic method for dL-griseofulvin and its 2-S-analogue

Masatoshi Yamato, Yasuo Takeuchi, Hideo Tomozane

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

An improved synthetic method for ifl-giseofulvin (4) and its 2'-S-analogue 8 has been developed. 7-Chloro-4,6-dimethoxy-2-[5-methoxy-l -methylthio-3-oxohexylidene]-3 (2H)-benzofuranone (7), prepared by reaction of the corresponding 3 (2H)-benzofur-anone with l,l-bis(methylthio)-5-methoxy-l-hexen-3-one (6), undergoes stereoselective intramolecular cyclization when treated with activated alumina in refluxing diethyl ether. The product, the 2'-5'-analogue of dl-griseofulvin 8, is converted to dl-griseofulvin (4) in good yield.

Original language	English
Pages (from-to)	569-570
Number of pages	2
Journal	Synthesis (Germany)
Volume	1990
Issue number	7
DOIs	https://doi.org/10.1055/s-1990-26942
Publication status	Published - Jan 1 1990

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1055/s-1990-26942

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title = "An improved synthetic method for dL-griseofulvin and its 2-S-analogue",

abstract = "An improved synthetic method for ifl-giseofulvin (4) and its 2'-S-analogue 8 has been developed. 7-Chloro-4,6-dimethoxy-2-[5-methoxy-l -methylthio-3-oxohexylidene]-3 (2H)-benzofuranone (7), prepared by reaction of the corresponding 3 (2H)-benzofur-anone with l,l-bis(methylthio)-5-methoxy-l-hexen-3-one (6), undergoes stereoselective intramolecular cyclization when treated with activated alumina in refluxing diethyl ether. The product, the 2'-5'-analogue of dl-griseofulvin 8, is converted to dl-griseofulvin (4) in good yield.",

author = "Masatoshi Yamato and Yasuo Takeuchi and Hideo Tomozane",

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T1 - An improved synthetic method for dL-griseofulvin and its 2-S-analogue

AU - Yamato, Masatoshi

AU - Takeuchi, Yasuo

AU - Tomozane, Hideo

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Y1 - 1990/1/1

N2 - An improved synthetic method for ifl-giseofulvin (4) and its 2'-S-analogue 8 has been developed. 7-Chloro-4,6-dimethoxy-2-[5-methoxy-l -methylthio-3-oxohexylidene]-3 (2H)-benzofuranone (7), prepared by reaction of the corresponding 3 (2H)-benzofur-anone with l,l-bis(methylthio)-5-methoxy-l-hexen-3-one (6), undergoes stereoselective intramolecular cyclization when treated with activated alumina in refluxing diethyl ether. The product, the 2'-5'-analogue of dl-griseofulvin 8, is converted to dl-griseofulvin (4) in good yield.

AB - An improved synthetic method for ifl-giseofulvin (4) and its 2'-S-analogue 8 has been developed. 7-Chloro-4,6-dimethoxy-2-[5-methoxy-l -methylthio-3-oxohexylidene]-3 (2H)-benzofuranone (7), prepared by reaction of the corresponding 3 (2H)-benzofur-anone with l,l-bis(methylthio)-5-methoxy-l-hexen-3-one (6), undergoes stereoselective intramolecular cyclization when treated with activated alumina in refluxing diethyl ether. The product, the 2'-5'-analogue of dl-griseofulvin 8, is converted to dl-griseofulvin (4) in good yield.

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