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Communication | Special issue | Vol 72, No. 1, 2007, pp.95-102
Published online, 28th November, 2006
DOI: 10.3987/COM-06-S(K)8
Total Synthesis of (-)- and ent-(+)-4-Desacetoxy-5-desethylvindoline

Hayato Ishikawa and Dale L. Boger*

*Department of Chemistry and, The Skaggs Institute for Chemcial Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, U.S.A.

Abstract

A concise synthesis of (-)- and ent-(+)-4-desacetoxy-5-desethylvindoline (2), a key analogue of vindoline, is disclosed enlisting an intramolecular tandem [4+2]/[3+2] cycloaddition cascade of 1,3,4-oxadiazole (5) to assemble the pentacyclic skeleton of 2 in a single step that forms three new rings, four C-C bonds, and sets all five key stereocenters. The subsequent efforts on the elaboration of 6 to 2 revealed two subtle features key to our recent total syntheses of vindoline, vindorosine, and related natural products based on this strategy.