Issue 16, 2014

Concise total synthesis of botryolide B

Abstract

An efficient total synthesis of botryolide B was achieved in 9 longest linear steps with 22% overall yield via esterification of a carboxylic acid with an alcohol fragment and a ring closing metathesis (RCM) reaction as pivotal steps to construct the macrolactone ring system. Our novel approach for the synthesis of the 2-alkene-1,5-diol fragment was achieved by a ring closing metathesis reaction followed by a reductive opening strategy, whereas the carboxylic acid fragment was accessed from commercially available (R)-(+)-α-hydroxy-γ-butyrolactone in three steps.

Graphical abstract: Concise total synthesis of botryolide B

Supplementary files

Article information

Article type
Paper
Submitted
19 Aug 2013
Accepted
02 Dec 2013
First published
04 Dec 2013

RSC Adv., 2014,4, 8335-8340

Concise total synthesis of botryolide B

D. K. Mohapatra, G. Umamaheshwar, M. M. Rao, D. Umadevi and J. S. Yadav, RSC Adv., 2014, 4, 8335 DOI: 10.1039/C3RA44478C

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