Issue 33, 2021

The formation of benzoxacin-3-ones via intramolecular Nicholas reactions and synthesis of 8-membered heliannuols

Abstract

The γ-carbonyl cations generated from propargyl ether-Co2(CO)6 complexes undergo intramolecular Nicholas reactions to give dehydrobenzoxacin-3-one-Co2(CO)6 complexes in good yields. Reductive decomplexation and subsequent manipulation allows the synthesis of (±)-heliannuol K methyl ether and the formal syntheses of (±)-heliannuol K, (±)-heliannuol A, and (−)-heliannuol L.

Graphical abstract: The formation of benzoxacin-3-ones via intramolecular Nicholas reactions and synthesis of 8-membered heliannuols

Supplementary files

Article information

Article type
Communication
Submitted
18 Jul 2021
Accepted
04 Aug 2021
First published
04 Aug 2021

Org. Biomol. Chem., 2021,19, 7152-7155

The formation of benzoxacin-3-ones via intramolecular Nicholas reactions and synthesis of 8-membered heliannuols

B. St. Onge and J. R. Green, Org. Biomol. Chem., 2021, 19, 7152 DOI: 10.1039/D1OB01395E

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