Efficient access to a dihydropyran-containing macrolidevia a transannular oxy-Michael reaction: total synthesis of (+)-aspergillide C?

Chemical Communications Pub Date: 2011-05-31 DOI: 10.1039/C1CC12114F

Abstract

The second-generation enantioselective total synthesis of aspergillide C, a new type of 14-membered macrolide isolated from a marine-derived fungus, has been accomplished in a longest linear sequence of 15 steps from a chiral building block in 19% overall yield employing the 6-exo-trig transannular oxy-Michael reaction as the key step.

Graphical abstract: Efficient access to a dihydropyran-containing macrolidevia a transannular oxy-Michael reaction: total synthesis of (+)-aspergillide C
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