Total Synthesis of (−)-Picrinine, (−)-Scholarisine C, and (+)-5-β-Methoxyaspidophylline

The first asymmetric total synthesis of three picrinine-type akuammiline alkaloids, (−)-picrinine, (−)-scholarisine C, and (+)-5-β-methoxyaspidophylline, has been accomplished. The synthesis features an efficient acid-promoted oxo-bridge ring-opening and further carbonyl O-cyclization to assemble th...

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Bibliographic Details
Published in:Organic letters 2021-09, Vol.23 (17), p.6836-6840
Main Authors: Zou, Peng, Yang, Hongjian, Wei, Jian, Wang, Taimin, Zhai, Hongbin
Format: Article
Language:English
Subjects:
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
Molecular Structure
Oxidation-Reduction
Stereoisomerism
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Summary:The first asymmetric total synthesis of three picrinine-type akuammiline alkaloids, (−)-picrinine, (−)-scholarisine C, and (+)-5-β-methoxyaspidophylline, has been accomplished. The synthesis features an efficient acid-promoted oxo-bridge ring-opening and further carbonyl O-cyclization to assemble the furoindoline scaffold, an unusual Dauben–Michno oxidation to construct the requisite α,β-unsaturated aldehyde functionality, and a nickel-mediated reductive Heck reaction to forge the [3.3.1]-azabicyclic core.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c02393