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Functionalization of diazotetronic acid and application in a stereoselective modular synthesis of pulvinone, aspulvinones A–E, G, Q and their analogues

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Abstract

A modular synthesis of aspulvinones A, B, C, D, E, G and the recently isolated aspulvinone Q was developed. The methodology features a highly stereoselective aldol condensation of diazotetronic acid with aldehydes to provide 5-arylidene diazotetronates. Subsequent catalytic intermolecular C–H insertion reactions of the arylidene tetronates with arenes provide a series of naturally occurring aspulvinones including aspulvinones C, D and Q which have not been synthesized before. Variation of the aldehyde and the arene components furnishes synthetic analogues of the aspulvinones.

Graphical abstract: Functionalization of diazotetronic acid and application in a stereoselective modular synthesis of pulvinone, aspulvinones A–E, G, Q and their analogues

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Publication details

The article was received on 26 Jun 2018, accepted on 09 Aug 2018 and first published on 10 Aug 2018


Article type: Paper
DOI: 10.1039/C8OB01511B
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Functionalization of diazotetronic acid and application in a stereoselective modular synthesis of pulvinone, aspulvinones A–E, G, Q and their analogues

    A. Manchoju, R. A. Annadate, L. Desquien and S. V. Pansare, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB01511B

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