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| - Convergent, Enantioselective Syntheses of GuanacastepenesA and E Featuring a Selective Cyclobutane Fragmentation1
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| - The evolution of a convergent strategy that led to efficient, enantioselective syntheses of bothnatural (+)- and unnatural (−)-guanacastepene E and formal total syntheses of (+)- and (−)-guanacastepeneA is described. A union of five- and six-membered ring intermediates by an efficient π-allyl Stille cross-coupling reaction was followed by an intramolecular enone-olefin [2 + 2] photocycloaddition and astereoelectronically controlled, reductive fragmentation of the resulting cyclobutyl ketone. The latter twotransformations 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-memberedring vinyl stannane from the monoterpene R-(−)-carvone featuring a carbon−carbon bond forming ringcontraction was also developed.
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