Absolute configuration of (+)-aureothin

A toxic metabolite possessing γ-pyrone unit

Y. Ishibashi, Shigeru Ohba, S. Nishiyama, S. Yamamura

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

The absolute configuration of aureothin (1) has been determined by synthesis of (-)-aureonone (4) bearing R-configuration. X-Ray single crystallographic analysis of 21 guaranteed the stereochemistry of the chiral center introduced by Sharpless asymmetric epoxidation, as well as that of isoaureothin (3) which was previously synthesized in a similar pathway. Aureothin (1) itself was also synthesized, although Wittig coupling reaction of 4 under basic conditions, caused a partial epimerization of the chiral center.

Original languageEnglish
Pages (from-to)3643-3649
Number of pages7
JournalBulletin of the Chemical Society of Japan
Volume68
Issue number12
DOIs
Publication statusPublished - 1995 Dec

Fingerprint

Pyrones
Poisons
Metabolites
Bearings (structural)
Stereochemistry
Epoxidation
X rays
aureothin

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Absolute configuration of (+)-aureothin : A toxic metabolite possessing γ-pyrone unit. / Ishibashi, Y.; Ohba, Shigeru; Nishiyama, S.; Yamamura, S.

In: Bulletin of the Chemical Society of Japan, Vol. 68, No. 12, 12.1995, p. 3643-3649.

Research output: Contribution to journalArticle

Ishibashi, Y. ; Ohba, Shigeru ; Nishiyama, S. ; Yamamura, S. / Absolute configuration of (+)-aureothin : A toxic metabolite possessing γ-pyrone unit. In: Bulletin of the Chemical Society of Japan. 1995 ; Vol. 68, No. 12. pp. 3643-3649.
@article{9bea690f39bc403d925f82d63a9a7534,
title = "Absolute configuration of (+)-aureothin: A toxic metabolite possessing γ-pyrone unit",
abstract = "The absolute configuration of aureothin (1) has been determined by synthesis of (-)-aureonone (4) bearing R-configuration. X-Ray single crystallographic analysis of 21 guaranteed the stereochemistry of the chiral center introduced by Sharpless asymmetric epoxidation, as well as that of isoaureothin (3) which was previously synthesized in a similar pathway. Aureothin (1) itself was also synthesized, although Wittig coupling reaction of 4 under basic conditions, caused a partial epimerization of the chiral center.",
author = "Y. Ishibashi and Shigeru Ohba and S. Nishiyama and S. Yamamura",
year = "1995",
month = "12",
doi = "10.1246/bcsj.68.3643",
language = "English",
volume = "68",
pages = "3643--3649",
journal = "Bulletin of the Chemical Society of Japan",
issn = "0009-2673",
publisher = "Chemical Society of Japan",
number = "12",

}

TY - JOUR

T1 - Absolute configuration of (+)-aureothin

T2 - A toxic metabolite possessing γ-pyrone unit

AU - Ishibashi, Y.

AU - Ohba, Shigeru

AU - Nishiyama, S.

AU - Yamamura, S.

PY - 1995/12

Y1 - 1995/12

N2 - The absolute configuration of aureothin (1) has been determined by synthesis of (-)-aureonone (4) bearing R-configuration. X-Ray single crystallographic analysis of 21 guaranteed the stereochemistry of the chiral center introduced by Sharpless asymmetric epoxidation, as well as that of isoaureothin (3) which was previously synthesized in a similar pathway. Aureothin (1) itself was also synthesized, although Wittig coupling reaction of 4 under basic conditions, caused a partial epimerization of the chiral center.

AB - The absolute configuration of aureothin (1) has been determined by synthesis of (-)-aureonone (4) bearing R-configuration. X-Ray single crystallographic analysis of 21 guaranteed the stereochemistry of the chiral center introduced by Sharpless asymmetric epoxidation, as well as that of isoaureothin (3) which was previously synthesized in a similar pathway. Aureothin (1) itself was also synthesized, although Wittig coupling reaction of 4 under basic conditions, caused a partial epimerization of the chiral center.

UR - http://www.scopus.com/inward/record.url?scp=0029621182&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0029621182&partnerID=8YFLogxK

U2 - 10.1246/bcsj.68.3643

DO - 10.1246/bcsj.68.3643

M3 - Article

VL - 68

SP - 3643

EP - 3649

JO - Bulletin of the Chemical Society of Japan

JF - Bulletin of the Chemical Society of Japan

SN - 0009-2673

IS - 12

ER -