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Studies Aimed at the Total Synthesis of the Antitumor Antibiotic Cochleamycin A. An Enantioselective Biosynthesis-Based Pathway to the AB Bicyclic Core

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journal contribution
posted on 19.12.2001, 00:00 by Jiyoung Chang, Leo A. Paquette
A convergent, highly enantioselective synthesis of the fully functionalized AB sector of cochleamycin A is described. A pair of building blocks, crafted from l-malic and l-ascorbic acids, are conjoined in a manner that gives rise to an (E,Z,E)-1,6,8-nonatriene. On heating, the latter undergoes stereocontrolled intramolecular Diels−Alder cyclization via an endo transition state.