Totally Synthetic by Paul H. Docherty, 2 May 2006
Total Synthesis of Machaeriol D
Q. Wang, Q. Huang, B. Chen, J. Lu, H. Wang, X. She, X. Pan, Angew. Chem. Int. Ed. 2006, 45, 3651-3653.
SN2′ action in this total synthesis of the 5,6-secohexahydrodibenzopyran Machaeriol D by She and Pan. Starting with materials readily available from literature syntheses, a few relatively simple transformations result in the precursors for the SN2′ process. They completed this in an anti fashion, resulting in the silyl enol ether in 80% yield as a single diastereoisomer. Good job!