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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| Published in: | Organic letters Vol. 26; no. 45; pp. 9689 - 9692 |
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| Main Authors: | , |
| Format: | Journal Article |
| Language: | English |
| Published: |
United States
American Chemical Society
15-11-2024
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| Subjects: | |
| Online Access: | Get full text |
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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. |
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| Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ISSN: | 1523-7060 1523-7052 1523-7052 |
| DOI: | 10.1021/acs.orglett.4c03445 |