Synthesis and stereochemical assignment of (+)-Cladospolide D

Please use this identifier to cite or link to this item: http://ir.lib.ncu.edu.tw/handle/987654321/28345

Title:	Synthesis and stereochemical assignment of (+)-Cladospolide D
Authors:	Lu,KJ;Chen,CH;Hou,DR
Contributors:	中央大學
Keywords:	RING-CLOSING METATHESIS;CHEMOENZYMATIC TOTAL-SYNTHESIS;MACROLIDE ANTIBIOTIC (-)-A26771B;ASYMMETRIC-SYNTHESIS;CROSS-METATHESIS;NATURAL-PRODUCTS;FORMAL SYNTHESIS;CLADOSPOLIDE-B;POLYKETIDE METABOLITES;CHIRAL SULFOXIDES
Date:	2009
Issue Date:	2010-06-29 19:46:38 (UTC+8)
Publisher:	化學研究所
Abstract:	Cladospolides A-D are 12-membered, alpha,beta-unsaturated lactones isolated from various species of Cladosporium. Cladospolide D is unique in its gamma-keto functionality and possesses antifungal activity; however, the stereochemistry of Cladoapolide D was unknown. We report the asymmetric syntheses to generate both possible diastereomers of Cladospolide D. Two regioselective cross-metatheses were applied to form the carbon skeleton, and the two olefins were differentiated by Michael addition, hydrogenation, and elimination. Later, the macrocycle was achieved through the Yamaguchi protocol. After comparing the spectroscopic data of the synthetic Cladospolide D with the reported values, the stereochemistry of Cladospolide D is confirmed as (2E,5R,11S). (C) 2008 Elsevier Ltd. All rights reserved.
Relation:	TETRAHEDRON
Appears in Collections:	[Graduate Institute of Chemistry] journal & Dissertation

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