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

Access to Document

10.1248/cpb.39.3048

Fingerprint Dive into the research topics of 'Intramolecular Michael Reaction in Diastereoselective Synthesis of dl-Griseofulvin'. Together they form a unique fingerprint.

Cite this

@article{e5b63cca2f71484d8f79df718ed3a5e0,

title = "Intramolecular Michael Reaction in Diastereoselective Synthesis of dl-Griseofulvin",

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.",

keywords = "chelation control, diastereoselective Michael reaction, dl-griseofulvin, reaction mechanism",

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

year = "1991",

doi = "10.1248/cpb.39.3048",

language = "English",

volume = "39",

pages = "3048--3050",

journal = "Chemical and Pharmaceutical Bulletin",

issn = "0009-2363",

publisher = "Pharmaceutical Society of Japan",

number = "11",

}

TY - JOUR

T1 - Intramolecular Michael Reaction in Diastereoselective Synthesis of dl-Griseofulvin

AU - Takeuchi, Yasuo

AU - Watanabe, Ikuo

AU - Tomozane, Hideo

AU - Hashigaki, Kuniko

AU - Yamato, Masatoshi

PY - 1991

Y1 - 1991

N2 - 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.

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

UR - http://www.scopus.com/inward/record.url?scp=0026328725&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0026328725&partnerID=8YFLogxK

U2 - 10.1248/cpb.39.3048

DO - 10.1248/cpb.39.3048

M3 - Article

AN - SCOPUS:0026328725

VL - 39

SP - 3048

EP - 3050

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

SN - 0009-2363

IS - 11

ER -

Intramolecular Michael Reaction in Diastereoselective Synthesis of dl-Griseofulvin

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Cite this