Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 130, Issue 18, Pages 6018-6024Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja800574m
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Funding
- NIGMS NIH HHS [R01 GM049093-16, P050-GM069663, P50 GM069663-06, R01 GM049093, GM-49093, P50 GM069663] Funding Source: Medline
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A tandem Diels-Alder/azido-Schmidt reaction sequence provides rapid access to the core skeleton shared by several Stemona alkaloids including stenine, neostenine, tuberostemonine, and neotuberostemonine. The discovery and evolution of inter- and intramolecular variations of this process and their applications to total syntheses of (+/-)-stenine and (+/-)-neostenine are described. The stereochemical outcome of the reaction depends on both substrate type and reaction conditions, enabling the preparation of both (+/-)-stenine and (+/-)-neostenine from the same diene/dienophile combination.
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