Synthesis 2019; 51(18): 3529-3535
DOI: 10.1055/s-0037-1611838
paper
© Georg Thieme Verlag Stuttgart · New York

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

Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, UT 84112, USA   Email: cakoto@hotmail.com
,
Jon D. Rainier
› Author Affiliations
We are grateful to the National Institutes of Health, General Medical Sciences (GM56677) for support of this work. C.O.A. acknowledges Pfizer for a graduate fellowship.
Further Information

Publication History

Received: 21 March 2019

Accepted after revision: 30 April 2019

Publication Date:
20 May 2019 (online)


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.

Supporting Information