Issue 29, 2024

A HMPA–H2O mediated oxygenative carbocyclization of 2-alkynylphenyl-substituted p-quinone methides to indenones

Abstract

Herein, we report a transition-metal and base-free protocol to access a wide range of functionalized indenone derivatives through a HMPA–H2O-mediated oxygenative annulation of 2-alkynylphenyl-substituted p-quinone methides. This method worked effectively for most of the p-QMs investigated and the corresponding indenone derivatives were obtained in moderate to good yields. This methodology was further extended to the formal synthesis of one of the resveratrol based natural products, (±)-isopaucifloral F.

Graphical abstract: A HMPA–H2O mediated oxygenative carbocyclization of 2-alkynylphenyl-substituted p-quinone methides to indenones

Supplementary files

Article information

Article type
Communication
Submitted
07 Jun 2024
Accepted
29 Jun 2024
First published
01 Jul 2024

Org. Biomol. Chem., 2024,22, 5891-5896

A HMPA–H2O mediated oxygenative carbocyclization of 2-alkynylphenyl-substituted p-quinone methides to indenones

S. Fatma, F. Ahmad, Y. A. Pankhade, P. K. Ranga and R. Vijaya Anand, Org. Biomol. Chem., 2024, 22, 5891 DOI: 10.1039/D4OB00966E

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