Intramolecular Michael Reaction in Diastereoselective Synthesis of dl-Griseofulvin

Yasuo Takeuchi; Ikuo Watanabe; Hideo Tomozane; Kuniko Hashigaki; Masatoshi Yamato

doi:10.1248/cpb.39.3048

Intramolecular Michael Reaction in Diastereoselective Synthesis of dl-Griseofulvin

Yasuo Takeuchi, Ikuo Watanabe, Hideo Tomozane, Kuniko Hashigaki, Masatoshi Yamato

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

1 Citation (Scopus)

Abstract

The diastereoselective cyclization of 2a to 5a, which was employed in our novel synthesis of dl-griseofulvin (7a), was studied in detail. It was found that the use of the metallic bases resulted in excellent diastereoselectively, whereas organic bases are ineffective for diastereoselective cyclization. Consequently, diastereoselective cyclization of 2 to 5 was proposed to proceed through the intramolecular Michael reaction under chelation control.

Original language	English
Pages (from-to)	3048-3050
Number of pages	3
Journal	Chemical and Pharmaceutical Bulletin
Volume	39
Issue number	11
DOIs	https://doi.org/10.1248/cpb.39.3048
Publication status	Published - 1991

Keywords

chelation control
diastereoselective Michael reaction
dl-griseofulvin
reaction mechanism

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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author = "Yasuo Takeuchi and Ikuo Watanabe and Hideo Tomozane and Kuniko Hashigaki and Masatoshi Yamato",

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AU - Yamato, Masatoshi

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AB - The diastereoselective cyclization of 2a to 5a, which was employed in our novel synthesis of dl-griseofulvin (7a), was studied in detail. It was found that the use of the metallic bases resulted in excellent diastereoselectively, whereas organic bases are ineffective for diastereoselective cyclization. Consequently, diastereoselective cyclization of 2 to 5 was proposed to proceed through the intramolecular Michael reaction under chelation control.

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KW - dl-griseofulvin

KW - reaction mechanism

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