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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 18
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Articles

Brønsted acid promoted intramolecular cyclization of O-alkynyl benzoic acids: Concise total synthesis of exserolide F

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Pages 2403-2408 | Received 25 Apr 2018, Accepted 17 Jun 2018, Published online: 17 Aug 2018
 

Abstract

Herein we report the stereoselective total synthesis of Exserolide F. The key step involves triflic acid catalyzed highly regioselective intramolecular cyclization of an O-alkynyl benzoic acid derivative to accomplish the core isocoumarin skeleton of the natural product via 6-endo-dig mode of cyclization. The other important steps are: Sharpless asymmetric epoxidation, Barbier propargylation, Sonogashira coupling en route to access the O-alkynyl benzoic acid derivative.

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Funding

M.D. and L.K are thankful to the UGC, New Delhi for the financial support in the form of fellowship.

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