The formation of benzoxacin-3-ones via intramolecular Nicholas reactions and synthesis of 8-membered heliannuols. Issue 33 (10th August 2021)

• Record Type: Journal Article
• Authors: St. Onge, Brent; Green, James R.
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 33(2021)
• Page Start: 7152
• Page End: 7155
• Publication Date: 2021-08-10
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob01395e
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Intramolecular Nicholas reactions have been shown to give dehydrobenzoxacin-3-one-Co2 (CO)6 complexes. This allows the synthesis of (±)-heliannuol K methyl ether and the formal syntheses of (±)-heliannuol K, (±)-heliannuol A, and (−)-heliannuol L. 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.