Asymmetric total synthesis of curacin A

Article abstract of DOI:10.1016/0040-4039(96)00860-X

Curacin A (1), a novel antimitotic agent, was synthesized in a highly stereo-controlled manner. The key steps were (1) an asymmetric allylation using a chiral allyltitanium reagent and a double-asymmetric Simmons-Smith cyclopropanation to introduce three chiral centers, (2) Wittig and Wittig- Horner reactions to construct the C(3-4) and C(7-10) alkenes, and (3) a direct conversion of the thiazolidine to the thiazoline.