期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 142, 期 12, 页码 5556-5561出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c01774
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资金
- JSPS KAKENHI [JP15H05841]
- Naito Foundation
- Waseda University
A convergent enantioselective total synthesis of cotylenin A is described. The A-ring fragment, prepared via the catalytic asymmetric intramolecular cyclopropanation developed in our laboratory, and the C-ring fragment, prepared from a known chiral compound via a modified acyl radical cyclization, were successfully assembled by the Utimoto coupling reaction. The formidable carbocyclic eight-membered ring of cotylenin A was efficiently constructed by a palladium-mediated cyclization. All the hydroxy groups in the scaffold were stereoselectively introduced, and a modified reducing reagent, Me4NBH((O2CPr)-Pr-i)(3), has been developed. The sugar moiety fragment was prepared via three consecutive carbon-oxygen bond-forming reactions, and the glycosylation was accomplished using Wan's protocol.
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