期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 53, 期 43, 页码 11634-11639出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201405609
关键词
alkaloids; dimerization; epoxidation; indole; total synthesis
资金
- NIH-NIGMS [GM074825]
- German Academic Exchange Service (DAAD)
We report an efficient and highly stereoselective strategy for the synthesis of Aspidosperma alkaloids based on the transannular cyclization of a chiral lactam precursor. Three new stereocenters are formed in this key step with excellent diastereoselectivity due to the conformational bias of the cyclization precursor, leading to a versatile pentacyclic intermediate. A subsequent stereoselective epoxidation followed by a mild formamide reduction enabled the first total synthesis of the Aspidosperma alkaloids (-)-mehranine and (+)-(6S,7S)-dihydroxy-N-methylaspidospermidine. A late-stage dimerization of (-)-mehranine mediated by scandium trifluoromethanesulfonate completed the first total synthesis of (-)-methylenebismehranine.
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