Synthesis of Noraugustamine and Development of an Oxidative Heck/Aza-Wacker Cascade Cyclization

Radical and transition metal-catalyzed cascade cyclization strategies were investigated with respect to the synthesis of the tetracyclic core of the augustamine-type Amaryllidaceae alkaloids. These studies resulted in the synthesis of noraugustamine and the development of an oxidative Heck/aza-Wacke...

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Bibliographic Details
Published in:Organic letters 2022-04, Vol.24 (16), p.3019-3023
Main Authors: Holman, Karli R, Stanko, Allison M, Richter, Matthieu J. R, Feng, Sean S, Gessesse, Mahideremariyam N, Reisman, Sarah E
Format: Article
Language:English
Subjects:
Amaryllidaceae Alkaloids - chemistry
Cyclization
Molecular Structure
Oxidation-Reduction
Oxidative Stress
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Summary:Radical and transition metal-catalyzed cascade cyclization strategies were investigated with respect to the synthesis of the tetracyclic core of the augustamine-type Amaryllidaceae alkaloids. These studies resulted in the synthesis of noraugustamine and the development of an oxidative Heck/aza-Wacker cascade forming two rings, a C–N bond, and an all-carbon quaternary center in a single step.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c00948