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Ylva E. Bergman

1 paper in the library · 21 citations · publishing 2009

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Total Synthesis of 20-Norsalvinorin A. 1. Preparation of a Key Intermediate

The Journal of Organic Chemistry February 20, 2009 Ylva E. Bergman, Roger Mulder, Patrick Perlmutter 21 citations

The key tricyclic intermediate 3a, for the total synthesis of the C(20)-nor analogue of salvinorin A, was prepared in seven steps from 3-furaldehyde. Key steps involved a highly regio- and diastereoselective Lewis acid assisted Diels-Alder reaction followed by base-promoted epimerization and a completely stereoselective conjugate reduction.