First asymmetric total synthesis of synerazol, an antifungal antibiotic, and determination of its absolute stereochemistry

Yujiro Hayashi; Mitsuru Shoji; Takasuke Mukaiyama; Hiroaki Gotoh; Shinpei Yamaguchi; Munetaka Nakata; Hideaki Kakeya; Hiroyuki Osada

doi:10.1021/jo050664x

First asymmetric total synthesis of synerazol, an antifungal antibiotic, and determination of its absolute stereochemistry

Yujiro Hayashi, Mitsuru Shoji, Takasuke Mukaiyama, Hiroaki Gotoh, Shinpei Yamaguchi, Munetaka Nakata, Hideaki Kakeya, Hiroyuki Osada

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

34 Citations (Scopus)

Abstract

By synthesizing two possible diastereomers, the first asymmetric total synthesis of synerazol, an antifungal antibiotic, has been accomplished, allowing determination of its absolute stereochemistry. A more practical second generation route was also established. The key steps are racemization-free deprotection of a TIPS group and introduction of a methyl ether by DMD oxidation of the benzylidene moiety in a substrate having a small protecting group.

Original language	English
Pages (from-to)	5643-5654
Number of pages	12
Journal	Journal of Organic Chemistry
Volume	70
Issue number	14
DOIs	https://doi.org/10.1021/jo050664x
Publication status	Published - 2005 Jul 8
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo050664x

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abstract = "By synthesizing two possible diastereomers, the first asymmetric total synthesis of synerazol, an antifungal antibiotic, has been accomplished, allowing determination of its absolute stereochemistry. A more practical second generation route was also established. The key steps are racemization-free deprotection of a TIPS group and introduction of a methyl ether by DMD oxidation of the benzylidene moiety in a substrate having a small protecting group.",

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AU - Hayashi, Yujiro

AU - Shoji, Mitsuru

AU - Mukaiyama, Takasuke

AU - Gotoh, Hiroaki

AU - Yamaguchi, Shinpei

AU - Nakata, Munetaka

AU - Kakeya, Hideaki

AU - Osada, Hiroyuki

PY - 2005/7/8

Y1 - 2005/7/8

N2 - By synthesizing two possible diastereomers, the first asymmetric total synthesis of synerazol, an antifungal antibiotic, has been accomplished, allowing determination of its absolute stereochemistry. A more practical second generation route was also established. The key steps are racemization-free deprotection of a TIPS group and introduction of a methyl ether by DMD oxidation of the benzylidene moiety in a substrate having a small protecting group.

AB - By synthesizing two possible diastereomers, the first asymmetric total synthesis of synerazol, an antifungal antibiotic, has been accomplished, allowing determination of its absolute stereochemistry. A more practical second generation route was also established. The key steps are racemization-free deprotection of a TIPS group and introduction of a methyl ether by DMD oxidation of the benzylidene moiety in a substrate having a small protecting group.

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First asymmetric total synthesis of synerazol, an antifungal antibiotic, and determination of its absolute stereochemistry

Abstract

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