Enantioselective synthesis of lepadins A D from a phenylglycinol-derived hydroquinolone lactam
The marine alkaloids (-)-lepadins A-C and (+)-lepadin D, belonging to two diastereoisomeric series, were synthesized from an (R)-phenylglycinol-derived tricyclic lactam via a common cis-decahydroquinoline intermediate. Crucial aspects of the synthesis are the stereochemical control in the assembly o...
| Authors: | , , , |
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| Format: | article |
| Status: | Versión aceptada para publicación |
| Publication Date: | 2015 |
| Country: | España |
| Institution: | Universidad de Barcelona |
| Repository: | Dipòsit Digital de la UB |
| OAI Identifier: | oai:diposit.ub.edu:2445/108026 |
| Online Access: | https://hdl.handle.net/2445/108026 |
| Access Level: | Open access |
| Keyword: | Alcaloides Lactames Compostos heterocíclics Síntesi asimètrica Alkaloids Lactams Heterocyclic compounds Asymmetric synthesis |
| Summary: | The marine alkaloids (-)-lepadins A-C and (+)-lepadin D, belonging to two diastereoisomeric series, were synthesized from an (R)-phenylglycinol-derived tricyclic lactam via a common cis-decahydroquinoline intermediate. Crucial aspects of the synthesis are the stereochemical control in the assembly of the cis-decahydroquinoline platform, in the introduction of the C2 methyl and C3 hydroxy substituents, and in the generation of the C5 stereocenter. |
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