期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 76, 期 11, 页码 4358-4370出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo2003506
关键词
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资金
- NSF [CHE-0503875]
- NIH-NIGMS [RO1 GM077309]
- NIH
- University of Kansas Honors Department
The first synthesis of dolabelide C (1), a cytotoxic marine macrolide, is reported utilizing a phosphate tether-mediated approach. Bicyclic phosphates (S,S,S-p)-5 and (R,R,R-p)-5 serve as the central building blocks for the construction of two major 1,3-anti-diol subunits in 1 through selective cleavage pathways, regioselective olefin reduction, and cross-metathesis. Overall, phosphate-mediated processes provided copious amounts of both major subunits allowing for a detailed RCM macrocyclization study to the 24-membered macrolactone 1.
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