期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 6, 页码 2191-2194出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201509602
关键词
aldol reaction; amino acids; Lycopodium alkaloids; Mannich reaction; total synthesis
资金
- NaturalSciences and Engineering Research Council of Canada
- [SFB 749]
Two amino acids play a key role in the first total synthesis of lycopalhineA. l-glutamic acid serves as a convenient chiral starting material for the 13-step synthesis, and l-proline promotes an unusual 5-endo-trig Mannich cyclization that generates the central pyrrolidine ring of the Lycopodium alkaloid. The bicyclo[3.3.0]octanol moiety of the molecule is formed through an intramolecular aldol addition that may occur spontaneously in nature.
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