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Synthesis of Leucascandrolide A via a Spontaneous Macrolactolization

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Department of Chemistry, University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637
Cite this: J. Am. Chem. Soc. 2002, 124, 46, 13670–13671
Publication Date (Web):October 24, 2002
https://doi.org/10.1021/ja028428g
Copyright © 2002 American Chemical Society
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Abstract

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We have developed a concise, convergent, and stereocontrolled synthesis of (±)-leucascandrolide A (18 steps from commercially available precursors), featuring a complete relay of the initial stereochemical information via a series of diastereoselective transformations. Spontaneous macrolactolization discovered during this synthetic exercise has provided unprecedented access to this macrolide and demonstrated the possibility of accessing even large-ring systems in a highly controlled and efficient manner.

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 To whom correspondence should be addressed. E-mail:  [email protected]

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