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Total Synthesis of (−)-Picrinine, (−)-Scholarisine C, and (+)-5-β-Methoxyaspidophylline by Peng Zou; Hongjian Yang; Jian Wei; Taimin Wang; Hongbin Zhai is a Chemistry article available to read on EtoBox.

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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.

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Author

Peng Zou; Hongjian Yang; Jian Wei; Taimin Wang; Hongbin Zhai

Publisher

American Chemical Society (ACS)

Published

2021

Language

EN

Field

Chemistry (Physical Sciences)