Asymmetric Total Syntheses of the Akuammiline Alkaloids (−)‐Strictamine and (−)‐Rhazinoline

Strictamine and rhazinoline are representative methanoquinolizidine‐containing akuammiline alkaloids that possess different stereochemistry at the C16 position. A unified approach to the enantioselective total syntheses of these two molecules is described. The key steps in this synthesis include a p...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-04, Vol.58 (18), p.6059-6063
Main Authors: Li, Wenfei, Chen, Zhitao, Yu, Di, Peng, Xin, Wen, Guohua, Wang, Siqi, Xue, Fei, Liu, Xiao‐Yu, Qin, Yong
Format: Article
Language:English
Subjects:
Alkaloids
Alkylation
Allyl compounds
Cascade chemical reactions
cascade reaction
Chemical reactions
Chemical synthesis
Enantiomers
Nickel
Palladium
photoredox catalysis
Stereochemistry
total synthesis
transition metal
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Summary:Strictamine and rhazinoline are representative methanoquinolizidine‐containing akuammiline alkaloids that possess different stereochemistry at the C16 position. A unified approach to the enantioselective total syntheses of these two molecules is described. The key steps in this synthesis include a photocatalytic intra/intermolecular type II radical cascade reaction, a Tsuji–Trost allylation, a palladium‐ or nickel‐mediated cyclization, and a late‐stage intramolecular N‐alkylation reaction. Unified syntheses of the challenging methanoquinolizidine‐containing akuammiline alkaloids (−)‐strictamine and (−)‐rhazinoline have been achieved in an enantioselective fashion employing photocatalytic cascade and transition‐metal‐mediated cyclization reactions as key steps.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201901074