Total Synthesis and Structure Revision of (±)-Clavilactone D Through Selective Cyclization of an α,β-Dicarbonyl Peroxide

5 years ago

Total Synthesis and Structure Revision of (±)-Clavilactone D Through Selective Cyclization of an α,β-Dicarbonyl Peroxide

Barry B. Snider, Zhiping Li, Leiyang Lv

The structure of (±)-clavilactone D was revised, and the synthesis was achieved in seven steps from a substituted benzaldehyde. The key step was the base-catalyzed cyclization of an α,β-carbonyl peroxide, which was obtained by an iron-catalyzed three-component reaction of a benzaldehyde, an alkene, and TBHP. NaBH₄-mediated reductive lactonization of the resulting cis-dicarbonyl epoxide led to the α,β-epoxy-γ-butyrolactone skeleton highly stereoselectively. The synthesis provides a concise, reliable, and practical route to the revised structure of clavilactone D.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00693

DOI: 10.1021/acs.joc.7b00693