期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 12, 期 6, 页码 1747-1753出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200500994
关键词
gambierol; glycosides; metathesis; natural products; total synthesis
资金
- NIGMS NIH HHS [GM56677] Funding Source: Medline
The preceding manuscript detailed our synthesis of the gambierol A-C and F-H ring precursors. Reported herein is a description of the coupling of the two precursors and the conversion of the coupled material into gambierol. Coupling of the subunits involved ester formation, enol ether RCM, and mixed thioketal formation and reduction. By employing this strategy we were able to bring highly advanced subunits into the coupling and, as a result, we were able to minimize the number of post-coupling transformations required to complete gambierol. At the completion of the synthesis, we generated 7.5 mg (1.5% overall yield) of (-)-gambierol in 44 steps (longest linear sequence).
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