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Synlett 1996; 1996(9): 833-836
DOI: 10.1055/s-1996-5624
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Intermolecular Carbonyl-Ene Approach to the Bicyclic Analogues of Enediyne Antibiotics, Neocarzinostatin, C-1027, and Kedarcidin: Highly Diastereoselective Carbonyl-Ene Reaction with an Alkyne-Cobalt Complex1

Koichi Mikami* , Feng Feng, Hiroyuki Matsueda, Akihiro Yoshida, David S. Grierson
  • *Department of Chemical Technology, Tokyo Institute of Technology, Meguro-ku, Tokyo 152, Japan, FAX 3 5734 2776, kmikami@o.cc.titech.ac.jp
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Publication Date:
31 December 2000 (online)

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The alkoxy(methyl)aluminum chloride promoted intermolecular carbonyl-ene reaction of a conjugated ynal enophile bearing terminal ester function with an alkyne-cobalt complexed ene component is found to be highly erythro-diastereoselective, producing a multi-functionalized product which can be efficiently elaborated to the enediyne cores of neocarzinostatin, C-1027, and kedarcidin.

carbonyl-ene reaction - alkyne-cobalt complex - diastereoselectivity - enediyne antibiotics