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Issue 41, 2014
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Regiodivergent and short total synthesis of calothrixins

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Abstract

The anionic annulation of MOM-protected furoindolone with 4-bromoquinoline followed by deprotection of the N-MOM group provides calothrixin B, whereas that with 3-bromoquinoline yields isocalothrixin B. The outcomes are explained by the divergence of the reaction mechanism from commonly perceived quinolyne intermediate. A sequence of addition–cyclization–elimination is proposed to account for the formation of calothrixin from 4-bromoquinoline.

Graphical abstract: Regiodivergent and short total synthesis of calothrixins

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Article information


Submitted
24 Jun 2014
Accepted
19 Aug 2014
First published
21 Aug 2014

Org. Biomol. Chem., 2014,12, 8196-8203
Article type
Paper

Regiodivergent and short total synthesis of calothrixins

D. Mal, J. Roy and K. Biradha, Org. Biomol. Chem., 2014, 12, 8196
DOI: 10.1039/C4OB01309C

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