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Pure Appl. Chem., 2005, Vol. 77, No. 7, pp. 1161-1169

Synthesis of leucascandrolide A

Ying Wang, Jelena Janjic and Sergey A. Kozmin

Department of Chemistry, University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60637, USA

Abstract: This paper describes a convergent and stereocontrolled synthesis of leucascandrolide A, a marine natural product that exhibits potent growth inhibition of mammalian and yeast cells. The approach features a substrate-directed relay of the stereochemical information via a series of highly diastereoselective transformations. Spontaneous macrolactolization discovered during this synthetic exercise has provided an unprecedented access to this marine macrolide and demonstrates a new tactic for assembling large-ring systems based on the thermodynamic preference of hemiacetalization.