Tetrahydropyrans and their derivatives are common subunits in both natural and unnatural compounds of biological significance. Herein we report the carbonyl ene reaction of bis-exocyclic enol ether equivalents. This bi-directional strategy provides for rapid increase in complexity about the central pyran core and can be used for the preparation of complex oxygen heterocycles. This approach provides rapid entry to unusual 4H-pyran derivatives and can be further applied to the synthesis of complex spiroketals. The scope and limitations of this method are presented and an approach toward the bis-spiroketal unit of the marine natural product spirastrellolide B is described.

Bi-directional extension of the tetrahydropyran framewor: Studies toward the synthesis of C26-C39 spirastrellolide B

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ACS Fall 2022

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