Tetrahedron
Tetrahedron
5 years ago

An efficient and stereoselective synthesis of obolactone via modified Evans' Aldol protocol

An efficient and stereoselective synthesis of obolactone via modified Evans' Aldol protocol
Stereocontrolled total synthesis of obolactone was achieved from trans-cinnamaldehyde. The key steps in this synthetic sequence are a asymmetric Mukaiyama Aldol, a Crimmins' modified Evans' Aldol reaction to introduce C2′ stereocentre, a nucleophilic addition of potassium salt of mono methyl malonate, a Z-olefination using Andos' modified Horner-Wadsworth-Emmons reagent to introduce Z-olefin at C3, C4 in the final lactone skeleton, and a tandem deprotection and lactonization.

Publisher URL: www.sciencedirect.com/science

DOI: S0040402017308141

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