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A flexible and unified strategy for syntheses of cladospolides A, B, C, and iso-cladospolide B

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Title A flexible and unified strategy for syntheses of cladospolides A, B, C, and iso-cladospolide B
 
Creator SI, D
SEKAR, NM
KALIAPPAN, KP
 
Subject RING-CLOSING METATHESIS
CHEMOENZYMATIC TOTAL-SYNTHESIS
STEREOSELECTIVE TOTAL-SYNTHESIS
HYDROLYTIC KINETIC RESOLUTION
EFFICIENT TOTAL-SYNTHESIS
MEDIUM-SIZED RINGS
OLEFIN METATHESIS
ORGANIC-SYNTHESIS
PHYTOTOXIC MACROLIDE
NATURAL-PRODUCTS
 
Description A simple, efficient and flexible strategy for the syntheses of cladospolides A-C and iso-cladospolide B is reported here. This strategy involves Julia-Kocienski olefination and Yamaguchi macrolactonization as key steps, starting from either D-ribose or suitable tartaric acid esters. Although our initial efforts towards cladospolide A involving a ring closing metathetic approach were not successful, changing the mode of ring closure and the use of Julia-Kocienski olefination for the construction of the key intermediate solved this issue and paved the way for the completion of total syntheses of this class of natural products.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2012-06-26T09:33:20Z
2012-06-26T09:33:20Z
2011
 
Type Article
 
Identifier ORGANIC & BIOMOLECULAR CHEMISTRY,9(20)6988-6997
1477-0520
http://dx.doi.org/10.1039/c1ob05787a
http://dspace.library.iitb.ac.in/jspui/handle/100/14297
 
Language English