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Synthesis of phytuberin. 4-endo-tet acid-catalyzed cyclization of alpha-hydroxy epoxides

AuthorsPrangé, Thierry; Rodríguez Morales, María S. ; Suárez, Ernesto
Issue Date1-May-2003
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 68(11): 4422-4431 (2003)
AbstractThe 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.
Description10 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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