Concise Seven-Membered Oxepene/Oxepane Synthesis – Structural Motifs in Natural and Synthetic Products

Author:

Osei Akoto Clement1ORCID,Rainier Jon D.

Affiliation:

1. Department of Chemistry, University of Utah

Abstract

This work outlines a suitable method for the synthesis of oxepane skeleton using iterative C-glycoside technology on the oxepene intermediate, which was synthesized utilizing Wilkinson’s catalyst [Rh(PPh3)3Cl] to generate the isomerized product in a linear synthetic manner. The central core of the oxepene motif was achieved via an olefin metathesis reaction using the Grubbs second-generation and Schrock catalysts. The synthesis of the functionalized oxepane having the desired adriatoxin E-ring relative stereochemistry was achieved starting from commercially available homopropargylic alcohol.

Funder

National Institutes of Health

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

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