Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 128, Issue 21, Pages 7025-7035Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja060847g
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- NIGMS NIH HHS [GM 065483] Funding Source: Medline
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The evolution of a convergent strategy that led to efficient, enantioselective syntheses of both natural (+)- and unnatural (-)- guanacastepene E and formal total syntheses of (+)- and (-)- guanacastepene A is described. A union of five- and six-membered ring intermediates by an efficient pi-allyl Stille cross-coupling reaction was followed by an intramolecular enone-olefin [2+2] photocycloaddition and a stereoelectronically controlled, reductive fragmentation of the resulting cyclobutyl ketone. The latter two transformations enabled controlled formation of the C-11 quaternary stereocenter and the central seven-membered ring of the guanacastepenes. An enantiospecific synthesis of the functionalized five-membered ring vinyl stannane from the monoterpene R-(-)-carvone featuring a carbon-carbon bond forming ring contraction was also developed.
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