Utilisation of L-quebrachitol in natural product synthesis. Total synthesis and absolute configuration of (-)-oudemansin X

Noritaka Chida, Ken Yamada, Seiichiro Ogawa

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

The stereoselective conversion of the naturally occurring optically active cyclitol, L-quebrachitol 2, into antifungal β-methoxyacrylate, oudemansin X 1 is described. This first total synthesis of 1 fully confirmed the proposed absolute configuration of the antibiotic and showed the importance of 2 as a versatile chiral starting material in natural product syntheses.

Original languageEnglish
Pages (from-to)1957-1962
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number17
Publication statusPublished - 1993

Fingerprint

Biological Products
Cyclitols
Anti-Bacterial Agents
oudemansin X
quebrachitol

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

@article{03651a25e83c401db23f2d380bfd063a,
title = "Utilisation of L-quebrachitol in natural product synthesis. Total synthesis and absolute configuration of (-)-oudemansin X",
abstract = "The stereoselective conversion of the naturally occurring optically active cyclitol, L-quebrachitol 2, into antifungal β-methoxyacrylate, oudemansin X 1 is described. This first total synthesis of 1 fully confirmed the proposed absolute configuration of the antibiotic and showed the importance of 2 as a versatile chiral starting material in natural product syntheses.",
author = "Noritaka Chida and Ken Yamada and Seiichiro Ogawa",
year = "1993",
language = "English",
pages = "1957--1962",
journal = "Journal of the Chemical Society. Perkin Transactions 1",
issn = "1472-7781",
publisher = "Chemical Society",
number = "17",

}

TY - JOUR

T1 - Utilisation of L-quebrachitol in natural product synthesis. Total synthesis and absolute configuration of (-)-oudemansin X

AU - Chida, Noritaka

AU - Yamada, Ken

AU - Ogawa, Seiichiro

PY - 1993

Y1 - 1993

N2 - The stereoselective conversion of the naturally occurring optically active cyclitol, L-quebrachitol 2, into antifungal β-methoxyacrylate, oudemansin X 1 is described. This first total synthesis of 1 fully confirmed the proposed absolute configuration of the antibiotic and showed the importance of 2 as a versatile chiral starting material in natural product syntheses.

AB - The stereoselective conversion of the naturally occurring optically active cyclitol, L-quebrachitol 2, into antifungal β-methoxyacrylate, oudemansin X 1 is described. This first total synthesis of 1 fully confirmed the proposed absolute configuration of the antibiotic and showed the importance of 2 as a versatile chiral starting material in natural product syntheses.

UR - http://www.scopus.com/inward/record.url?scp=37049076629&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=37049076629&partnerID=8YFLogxK

M3 - Article

SP - 1957

EP - 1962

JO - Journal of the Chemical Society. Perkin Transactions 1

JF - Journal of the Chemical Society. Perkin Transactions 1

SN - 1472-7781

IS - 17

ER -