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Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/16752
Title: Synthesis of phytuberin. 4-endo-tet acid-catalyzed cyclization of alpha-hydroxy epoxides
Authors: Prangé, Thierry; Rodríguez Morales, María S.; Suárez, Ernesto
Issue Date: 1-May-2003
Publisher: American Chemical Society
Citation: Journal of Organic Chemistry 68(11): 4422-4431 (2003)
Abstract: The total synthesis of phytuberin, a phytoalexin of the Solanum genus, from (−)-α-santonin is reported. The key steps include (a) reductive cleavage of the C−O bond of the γ-lactone with concomitant protection of the C1 double bond, (b) Sharpless stereocontrolled hydroxy-assisted epoxidation of allylic alcohol 6 and simultaneous deprotection of the C1 double bond, (c) a rare 4-endo-tet acid-catalyzed cyclization of an α-hydroxy epoxide, and (d) an unprecedented 4-exo selenocyclization of a homoallylic alcohol.
Description: 10 pages, 7 schemes.-- PMID: 12762747 [PubMed].-- Printed version published May 30, 2003.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/jo034129d
Publisher version (URL): http://dx.doi.org/10.1021/jo034129d
URI: http://hdl.handle.net/10261/16752
ISSN: 0022-3263
DOI: 10.1021/jo034129d
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