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

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/Ph 3P...

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Bibliographic Details
Published in:Tetrahedron letters 1996-09, Vol.37 (40), p.7167-7170
Main Authors: Lai, Jing-Yu, Yu, Jurong, Mekonnen, Belew, Falck, J.R.
Format: Article
Language:English
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Summary: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/Ph 3P/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.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(96)01616-4