A Shimizu non-aldol approach to the formal total synthesis of palmerolide A

Pujari, Sandip A. ; Gowrisankar, Parthasarathy ; Kaliappan, Krishna P. (2011) A Shimizu non-aldol approach to the formal total synthesis of palmerolide A Chemistry - An Asian Journal, 6 (11). pp. 3137-3151. ISSN 1861-4728

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/asia.20...

Related URL: http://dx.doi.org/10.1002/asia.201100429

Abstract

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.

Item Type:Article
Source:Copyright of this article belongs to John Wiley and Sons, Inc.
Keywords:Julia–Kocienski Reaction; Macrolides; Melanoma; Ring-Closing Metathesis; Yamaguchi Esterification
ID Code:104993
Deposited On:19 May 2017 09:35
Last Modified:19 May 2017 09:35

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