Convergent, enantioselective syntheses of guanacastepenes A and E featuring a selective cyclobutane fragmentation

被引：0
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作者：
Shipet, William D. [1 ,2 ]
Sorensen, Erik J. [1 ]
机构：
[1] Frick Chemical Laboratory, Princeton University, Princeton, NJ 08544-1009, United States
[2] Merck Research Laboratories, West Point, PA, United States
来源：
Journal of the American Chemical Society | 2006年 / 128卷 / 21期
关键词：
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 π-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. © 2006 American Chemical Society;
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Journal article (JA)
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页码：7025 / 7035
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