Catalytic epoxypolyene cyclization via radicals: Highly diastereoselective formal synthesis of puupehedione and 8-epi-puupehedione

A catalytic and highly stereoselective synthesis of a common building block for the marine natural product puupehedione (1) and its biologically more active 8-epimer is described. Our approach features a copper-catalyzed allylic substitution reaction of epoxyfarnesyl acetate and a diastereoselective...

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Bibliographic Details
Published inSynlett no. 6; pp. 927 - 929
Main Authors Gansauer, A, Rosales, A, Justicia, J
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 04.04.2006
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
epoxypolyene cyclization
catalysis
TERPENOIDS
STRAIGHTFORWARD SYNTHESIS
MARINE SPONGE
natural products
DIHYDROXYLATION
cuprates
PUUPEHENONE
INHIBITORS
ENANTIOSELECTIVE TOTAL-SYNTHESIS
EFFICIENT
METABOLITE
STRUCTURE REVISION
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Summary:A catalytic and highly stereoselective synthesis of a common building block for the marine natural product puupehedione (1) and its biologically more active 8-epimer is described. Our approach features a copper-catalyzed allylic substitution reaction of epoxyfarnesyl acetate and a diastereoselective titanocene-catalyzed epoxypolyene cyclization via radicals. The formal syntheses of 1 and 2 are completed by highly diastereoselective ring closures to the required benzodihydropyran units.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2006-933139