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 journalArticle

31 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 languageEnglish
Pages (from-to)5643-5654
Number of pages12
JournalJournal of Organic Chemistry
Volume70
Issue number14
DOIs
Publication statusPublished - 2005 Jul 8
Externally publishedYes

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Methyl Ethers
Stereochemistry
Antifungal Agents
Oxidation
Substrates
synerazol

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Hayashi, Y., Shoji, M., Mukaiyama, T., Gotoh, H., Yamaguchi, S., Nakata, M., ... Osada, H. (2005). First asymmetric total synthesis of synerazol, an antifungal antibiotic, and determination of its absolute stereochemistry. Journal of Organic Chemistry, 70(14), 5643-5654. https://doi.org/10.1021/jo050664x

First asymmetric total synthesis of synerazol, an antifungal antibiotic, and determination of its absolute stereochemistry. / Hayashi, Yujiro; Shoji, Mitsuru; Mukaiyama, Takasuke; Gotoh, Hiroaki; Yamaguchi, Shinpei; Nakata, Munetaka; Kakeya, Hideaki; Osada, Hiroyuki.

In: Journal of Organic Chemistry, Vol. 70, No. 14, 08.07.2005, p. 5643-5654.

Research output: Contribution to journalArticle

Hayashi, Y, Shoji, M, Mukaiyama, T, Gotoh, H, Yamaguchi, S, Nakata, M, Kakeya, H & Osada, H 2005, 'First asymmetric total synthesis of synerazol, an antifungal antibiotic, and determination of its absolute stereochemistry', Journal of Organic Chemistry, vol. 70, no. 14, pp. 5643-5654. https://doi.org/10.1021/jo050664x
Hayashi, Yujiro ; Shoji, Mitsuru ; Mukaiyama, Takasuke ; Gotoh, Hiroaki ; Yamaguchi, Shinpei ; Nakata, Munetaka ; Kakeya, Hideaki ; Osada, Hiroyuki. / First asymmetric total synthesis of synerazol, an antifungal antibiotic, and determination of its absolute stereochemistry. In: Journal of Organic Chemistry. 2005 ; Vol. 70, No. 14. pp. 5643-5654.
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