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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Published inTetrahedron letters Vol. 37; no. 40; pp. 7167 - 7170
Main Authors Lai, Jing-Yu, Yu, Jurong, Mekonnen, Belew, Falck, J.R.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 30.09.1996
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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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