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Closed Access item 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
Appears in Collections:(IPNA) Artículos

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