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A Shimizu Non-Aldol Approach to the Formal Total Synthesis of Palmerolide A

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Title A Shimizu Non-Aldol Approach to the Formal Total Synthesis of Palmerolide A
 
Creator PUJARI, SA
GOWRISANKAR, P
KALIAPPAN, KP
 
Subject RING-CLOSING METATHESIS
MODIFIED JULIA OLEFINATION
MARINE NATURAL-PRODUCT
MEDIUM-SIZED RINGS
C-ARYL GLYCOSIDES
STEREOSELECTIVE-SYNTHESIS
ASYMMETRIC EPOXIDATION
ORGANIC-SYNTHESIS
REVISED STRUCTURES
VERSATILE APPROACH
Julia-Kocienski reaction
macrolides
melanoma
ring-closing metathesis
Yamaguchi esterification
 
Description A formal total synthesis of palmerolide A has been accomplished by assembling three fragments by means of successive Julia-Kocienski olefination, Yamaguchi esterification, and ring-closing metathesis (RCM). Our initial efforts to combine the first two fragments through a Julia-Kocienski reaction between a secondary sulfone and a ketone were not successful; nevertheless, it was feasible between a primary sulfone and aldehyde. Yamaguchi esterification with the third fragment then set the stage for a RCM reaction. Initial failure of the RCM with a PMB-ether adjacent to the olefins and the difficulty in cleaving the PMB-ether prompted us to change the choice of protecting groups, which then paved the way to the macrocyclic core of palmerolide A.
 
Publisher WILEY-BLACKWELL
 
Date 2012-06-26T04:42:56Z
2012-06-26T04:42:56Z
2011
 
Type Article
 
Identifier CHEMISTRY-AN ASIAN JOURNAL,6(11)3137-3151
1861-4728
http://dx.doi.org/10.1002/asia.201100429
http://dspace.library.iitb.ac.in/jspui/handle/100/13891
 
Language English