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Issue 23, 2014
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A concise approach for the synthesis of bitungolides: total syntheses of (−)-bitungolide B & E

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Abstract

The first total synthesis of (−)-bitungolide B and a second-generation total synthesis of (−)-bitungolide E are described. The cornerstone of the approach comprises a convergent and flexible route involving Brown crotylation, highly diastereoselective substrate controlled Paterson anti-aldol reaction, hydroxyl-directed 1,3-syn/anti reduction, Barton–McCombie deoxygenation and RCM reactions. Via this route, a common intermediate 13 is readily accessible for the synthesis of the family of bitungolides A–E and franklinolides A–C.

Graphical abstract: A concise approach for the synthesis of bitungolides: total syntheses of (−)-bitungolide B & E

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Publication details

The article was received on 03 Feb 2014, accepted on 25 Mar 2014 and first published on 25 Mar 2014


Article type: Paper
DOI: 10.1039/C4OB00250D
Citation: Org. Biomol. Chem., 2014,12, 4002-4012
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    A concise approach for the synthesis of bitungolides: total syntheses of (−)-bitungolide B & E

    K. M. Reddy, J. Shashidhar and S. Ghosh, Org. Biomol. Chem., 2014, 12, 4002
    DOI: 10.1039/C4OB00250D

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