Total Synthesis of (−)-Aspidospermidine via an Enantioselective Palladium-Catalyzed Allylic Substitution Strategy

A total synthesis of (−)-aspidospermidine via an enantioselective Pd-catalyzed allylic substitution strategy is reported. This represents the first application of a Pd-catalyzed allylic substitution with a 3-substituted indole derivative in the synthesis of Aspidosperma alkaloids. In our synthetic r...

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Bibliographic Details
Published in:Organic letters 2024-10, Vol.26 (45), p.9689-9692
Main Authors: O’Donnell, Charlotte R., Stark, Christian B. W.
Format: Article
Language:English
Subjects:
Aspidosperma
diastereoselectivity
enantioselective synthesis
enantioselectivity
indoles
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Summary:A total synthesis of (−)-aspidospermidine via an enantioselective Pd-catalyzed allylic substitution strategy is reported. This represents the first application of a Pd-catalyzed allylic substitution with a 3-substituted indole derivative in the synthesis of Aspidosperma alkaloids. In our synthetic route, the allylic substitution reaction was the stereo defining step. The pentacyclic framework was then constructed in a fully diastereoselective sequence. This culminated in the shortest enantioselective synthesis of aspidospermidine reported to date, in seven linear steps.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c03445