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The First Total Synthesis of Topsentolide B3

✍ Scribed by Eppakayala Sreedhar; Arramshetti Venkanna; Nagula Chandramouli; K. Suresh Babu; Janaswamy Madhusudana Rao

Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
227 KB
Volume
2011
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

The first total synthesis of the cytotoxic oxylipin Topsentolide B~3~ has been accomplished in 15 steps with an overall yield of 24 %. Starting with readily available cis‐butene diol as a synthon, the synthesis involved Marouka allylation and Sharpless hydroxylation for the construction of three asymmetric centers. The nine‐membered lactone ring was built through a selective Grubbs ring‐closing metathesis reaction. Other key steps in the synthesis are Cu^I^‐mediated alkynylation and Swern oxidation reactions. This provides a unique approach to the synthesis of oxylipins and offers the advantages of brevity and relatively high overall yield.

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