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Issue 21, 2013
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Total synthesis and biological evaluation of (−)-exiguolide analogues: importance of the macrocyclic backbone

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Abstract

(−)-Exiguolide (1), isolated from the marine sponge Geodia exigua, has been shown to inhibit the growth of the A549 human lung adenocarcinoma and NCI-H460 human lung large cell carcinoma cells in vitro. In this study, we synthesized structural analogues of 1 to explore its skeletal structure–activity relationships and found that the C18 methyl group and the configuration of the C16–C17 double bond of 1 are important for the potent antiproliferative activity. Furthermore, we prepared a series of side-chain analogues of 1 by diversification of a late-stage intermediate of our total synthesis, and found that the triene side chain of 1 could be modified to some extent without significant loss of activity, provided a Lewis basic heteroatom is placed at the terminus.

Graphical abstract: Total synthesis and biological evaluation of (−)-exiguolide analogues: importance of the macrocyclic backbone

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Article information


Submitted
22 Jan 2013
Accepted
13 Mar 2013
First published
14 Mar 2013

Org. Biomol. Chem., 2013,11, 3442-3450
Article type
Paper

Total synthesis and biological evaluation of (−)-exiguolide analogues: importance of the macrocyclic backbone

H. Fuwa, K. Mizunuma, M. Sasaki, T. Suzuki and H. Kubo, Org. Biomol. Chem., 2013, 11, 3442
DOI: 10.1039/C3OB40131F

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