Model studies on total synthesis of the chartellines, spirocyclic β-lactam alkaloids from a marine bryozoan
✍ Scribed by Xichen Lin; Steven M Weinreb
- Publisher
- Elsevier Science
- Year
- 2001
- Tongue
- French
- Weight
- 66 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A chartelline alkaloid model system containing a spirocyclic b-lactam moiety and a,b-unsaturated imine has been constructed from isatin using a Staudinger imine-ketene cycloaddition and an addition to an N-activated g-lactam as key steps.
📜 SIMILAR VOLUMES
A strategy for synthesis of the chartellamide marine alkaloids has been tested in a model, leading to the polycyclic ring system of the natural product, but which unfortunately does not provide the requisite C-9,20 relative stereochemistry.
Discorhabdins and prianosins have been isolated from marine sponges such as New Zealand sponges of the genus Latrunculia, Okinawan sponge Prianos melanos, and Fijian sponge Zyzzya cf. Marsailis. Among the various discorhabdins (A ± R) isolated, discorhabdins A (1), [1a,b,d] B, [1b] D, [1c] Q, [1e] a