期刊
NATURAL PRODUCT RESEARCH
卷 22, 期 13, 页码 1176-1188出版社
TAYLOR & FRANCIS LTD
DOI: 10.1080/14786410701838205
关键词
Amaryllidaceae alkaloids; (-)-gamma-Lycorane; Asymmetric induction; 5-Endo-trig cyclization
An asymmetric induction using (S)-1-arylethylamine-based chiral auxiliary and two Bu3SnH-mediated radical cyclisations have been developed for a total synthesis of (-)-gamma-lycorane (1). The first cyclisation proceeded in 5-endo-trig manner with moderate diastereoselectivtiy to give (3aR,7aR)-octahydroindol-2-one 6b as the major product using alpha-iodo-N-(6-oxocyclohexen-1-yl)-N-[(S)-1-phenylethyl] acetamide (5b). In the second cyclisation, the radical precursor 8 was used as substrate to construct the optically active lycorane skeleton 15 which was reduced using LiAlH4 into (-)-gamma-lycorane (1).
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