The combination of cross-metathesis and intramolecular oxa-Michael addition presents a seemingly simple approach to the synthesis of 2,6-disubstituted tetrahydropyrans. Under carefully chosen conditions, the reaction can deliver either the 2,6-<i>cis</i> or the 2,6-<i>trans</i> isomer with high selectivity. We have shown that usefulness of this chemistry and demonstrated its scope in syntheses of diospongin, curvulone, clavosolide and cyanolide, as well as in work towards bistramide and neopeltolide. In the course of our work, we have also developed a new, protecting group with enhanced Lewis acid stability: 2-chlorobenzyl.

Stereoselective synthesis of tetrahydropyranyl natural products by oxa-Michael addition

251st National Meeting (2016)

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