A Scalable Total Synthesis of (−)-Nakadomarin A
| Autor: | Hui Wang, Robert K. Boeckman, Ke Chen, Nathan E. Genung, Kyle W. Rugg, Todd R. Ryder |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_classification
Bicyclic molecule 010405 organic chemistry Stereochemistry Organic Chemistry Total synthesis 010402 general chemistry 01 natural sciences Biochemistry Aldehyde Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Furan Michael reaction Lactam Physical and Theoretical Chemistry Retrosynthetic analysis |
| Zdroj: | Organic Letters. 18:6136-6139 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.6b03137 |
| Popis: | The convergent total synthesis of the manzamine alkaloid (−)-nakadomarin A (1) is described. The retrosynthetic analysis recognized spirocycle 3, assembled via an organocatalyst-promoted Michael addition/cyclization between bicyclic lactam 4 and furan aldehyde 5, both accessible from achiral starting materials and on a multigram scale. Lactam 4 is assembled through an SN2′/reduction/Staudinger/retro-aza-Claisen sequence on scale. After spirocyclization, the synthesis of nakadomarin is completed in only six steps. |
| Databáze: | OpenAIRE |
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