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

研究成果 › 査読

1 被引用数 (Scopus)

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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.

本文言語	English
ページ（範囲）	3048-3050
ページ数	3
ジャーナル	Chemical and Pharmaceutical Bulletin
巻	39
号	11
DOI	https://doi.org/10.1248/cpb.39.3048
出版ステータス	Published - 1991

ASJC Scopus subject areas

化学 (全般)
創薬

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10.1248/cpb.39.3048

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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.

KW - chelation control

KW - diastereoselective Michael reaction

KW - dl-griseofulvin

KW - reaction mechanism

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Intramolecular Michael Reaction in Diastereoselective Synthesis of dl-Griseofulvin

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