期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2010, 期 9, 页码 1660-1668出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200901422
关键词
Total synthesis; Alkaloids; Fasicularin; Lepadiformine A; Zinc; Allylation
资金
- National Natural Science Foundation of China [20172064, 203900502, 20532040, 20525208]
- Basic Research Program of China [973]
The stereoselective total synthesis of fasicularin (1) and lepadiformine A (2) is described, which features the utilization of a Zn-mediated allylation of a chiral, aliphatic, N-tert-butanesulfinyl ketimine to construct the amino-substituted quaternary carbon center in good yield and with excellent diastereoselectivity. The azaspirocyclic scaffold was installed sequentially by a Sharp less dihydroxylation and an internal epoxide-opening reaction, and this scaffold was further converted into common intermediate 5. Removing the tosyl (Ts) protecting group of 5 and reductively aminating using Luche's reagent completed the synthesis of (-)-fasicularin (1), while reducing 5 using L-selectride, deprotecting the Ts group, and finishing with an intramolecular amino alcohol cyclocondensation completed the total synthesis of (-)-lepadiformine A (2).
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