Journal of the American Chemical Society 2004-10-13

Enantioselective total synthesis of (+)-gigantecin: exploiting the asymmetric glycolate aldol reaction.

Michael T Crimmins, Jin She

Index: J. Am. Chem. Soc. 126(40) , 12790-1, (2004)

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Abstract

The enantioselective synthesis of the potent, selective, cytotoxic, annonaceous acetogenin, (+)-gigantecin, has been completed. An asymmetric glycolate aldol serves to establish the stereocenters at C13,14 and at C21,22. A Carreira asymmetric acetylide addition is used to establish the C17 stereocenter.