Elsevier

Tetrahedron Letters

Volume 37, Issue 40, 30 September 1996, Pages 7167-7170
Tetrahedron Letters

Synthesis of curacin A, an antimitotic cyclopropane-thiazoline from the marine cyanobacterium Lyngbya majuscula

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Abstract

Charette asymmetric cyclopropanation, chiral thiazoline synthesis by thioamide cyclization under modified Mitsunobu conditions, Ti(iPrO)4/bi-naphthol catalyzed allylstannane addition, and an exceptionally mild two-carbon homologation via dehydrative alkylation with phenylsulfonylacetonitrile/Ph3P/ADDP convened in an efficient, stereocontrolled route to the title bioactive heterocycle.

Charette cyclopropanation, thioamide to thiazoline conversion, and Mitsunobu dehydrative alkylation with phenylsulfonylacetonitrile were exploited for a versatile, stereocontrolled synthesis of the title lipid.

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