期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 130, 期 41, 页码 13765-13770出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja8048207
关键词
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资金
- National Institutes of Health [CA28824, HL61401, CA062948]
- NSF [CHE-0619638]
A convergent, stereocontrolled route to either antipode of the cell adhesion inhibitor, peribysin E, has been achieved from carvone. Highlights of the synthesis include a Diels-Alder reaction to generate a cis-decalin framework, followed by semi pinacol-type ring contraction to secure the stereochemistry of the C-7 quaternary center. Potential mechanistic pathways for the critical ring contraction were studied through deuterium incorporation studies. In addition, an optimized olefin isomerization/Saegusa oxidation protocol is described for the conversion of [4+2] cycloadducts of 2-(trialkylsilyloxy)-1,3-dienes to 1,6(2H,7H)-naphthalenediones, having stereochemical arrangements not accessible via conventional Robinson annulation protocols. Finally, the ability to independently prepare either enantiomer of peribysin E from the corresponding antipode of carvone led to a reassignment of the absolute configuration of peribysin E.
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