Toward the total synthesis of (±)-andrastin C

Rei Okamoto; Kazutaka Takeda; Hidetoshi Tokuyama; Masataka Ihara; Masahiro Toyota

doi:10.1021/jo301948h

Toward the total synthesis of (±)-andrastin C

Rei Okamoto, Kazutaka Takeda, Hidetoshi Tokuyama, Masataka Ihara, Masahiro Toyota

PHA - Molecular Pharmaceutical Science

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

21 Citations (Scopus)

Abstract

An efficient approach to generate a fully functionalized cyclopenta[a]phenanthrene 34, the basic carbon framework of andrastin C (1c), is described. The present synthetic route features a stereoselective intramolecular Diels-Alder reaction of triene 12 and an intramolecular carbonyl ene reaction of 3-phenanthrenyl-2- (methoxymethoxy)propanal 31.

Original language	English
Pages (from-to)	93-103
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	78
Issue number	1
DOIs	https://doi.org/10.1021/jo301948h
Publication status	Published - 2013 Jan 4

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo301948h

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abstract = "An efficient approach to generate a fully functionalized cyclopenta[a]phenanthrene 34, the basic carbon framework of andrastin C (1c), is described. The present synthetic route features a stereoselective intramolecular Diels-Alder reaction of triene 12 and an intramolecular carbonyl ene reaction of 3-phenanthrenyl-2- (methoxymethoxy)propanal 31.",

author = "Rei Okamoto and Kazutaka Takeda and Hidetoshi Tokuyama and Masataka Ihara and Masahiro Toyota",

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AU - Okamoto, Rei

AU - Takeda, Kazutaka

AU - Tokuyama, Hidetoshi

AU - Ihara, Masataka

AU - Toyota, Masahiro

PY - 2013/1/4

Y1 - 2013/1/4

N2 - An efficient approach to generate a fully functionalized cyclopenta[a]phenanthrene 34, the basic carbon framework of andrastin C (1c), is described. The present synthetic route features a stereoselective intramolecular Diels-Alder reaction of triene 12 and an intramolecular carbonyl ene reaction of 3-phenanthrenyl-2- (methoxymethoxy)propanal 31.

AB - An efficient approach to generate a fully functionalized cyclopenta[a]phenanthrene 34, the basic carbon framework of andrastin C (1c), is described. The present synthetic route features a stereoselective intramolecular Diels-Alder reaction of triene 12 and an intramolecular carbonyl ene reaction of 3-phenanthrenyl-2- (methoxymethoxy)propanal 31.

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Toward the total synthesis of (±)-andrastin C

Abstract

ASJC Scopus subject areas

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