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Paper | Special issue | Vol 70, No. 1, 2006, pp.223-233
Published online, 29th August, 2006
DOI: 10.3987/COM-06-S(W)12
A De Novo Asymmetric Approach to Achiral Deoxy-Melodorinol Analogues

Md. Moinuddin Ahmed, Novruz Akhmedov, Hu Cui, Dirk Friedrich, and George A. O’Doherty*

*Department of Chemistry, West Virginia University, Morgantown, WV 26506-6045, U.S.A.

Abstract

A short and highly efficient route to deoxy-Melodorinol analogues has been developed. The key to the overall transformation is the use of an enantioselective Sharpless asymmetric dihydroxylation of an (Z,E)-dienoate to control the regioselectivity of the dihydroxylation reaction and a Mitsunobu elimination reaction to control the E-stereochemistry of the γ,δ-double bond. The highly efficient synthesis stereoselectively prepared four analogues in 3 steps from 4-substituted crotonaldehydes.