Journal
ORGANIC LETTERS
Volume 4, Issue 9, Pages 1515-1517Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol025746b
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- NCRR NIH HHS [S10-RR13673] Funding Source: Medline
- NIGMS NIH HHS [GM59384, GM60003] Funding Source: Medline
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The intramolecular [4 + 2]-cycloaddition of a 2-methylthio-5-amidofuran was used to create the azepinoindole skeleton present in the Stemona alkaloid stenine. The rearranged cycloadduct was converted to stenine (1) in 11 additional steps via a sequence that features a Crabtree catalyst directed hydrogenation (9-->10), iodolactonization (2-->11), and a Keck allylation (11-->12).
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