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

Clement Osei Akoto; Jon D. Rainier

doi:10.1055/s-0037-1611838

Synthesis, Table of Contents

Synthesis 2019; 51(18): 3529-3535
DOI: 10.1055/s-0037-1611838

paper

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

Clement Osei Akoto *

Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, UT 84112, USA Email: cakoto@hotmail.com

,

Jon D. Rainier

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Abstract

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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.

Key words

oxepane - oxepene - Wilkinson’s catalyst - metathesis - adriatoxin - yessotoxin - epoxidation

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References

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