The formation of benzoxacin-3-ones via intramolecular Nicholas reactions and synthesis of 8-membered heliannuols†
Brent St. Onge,James R. Green
Organic & Biomolecular Chemistry Pub Date : 08/04/2021 00:00:00 , DOI:10.1039/D1OB01395E
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