A Shimizu Non-Aldol Approach to the Formal Total Synthesis of Palmerolide A
DSpace at IIT Bombay
View Archive InfoField | Value | |
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
|
|