Absolute Configuration of (+)-Aureothin: A Toxic Metabolite Possessing γ-Pyrone Unit
- 1 December 1995
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 68 (12) , 3643-3649
- https://doi.org/10.1246/bcsj.68.3643
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.Keywords
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