N-acyldihydropyridones as synthetic intermediates. A short synthesis of (±)-pumiliotoxin C.
✍ Scribed by Daniel L. Comins; Ali Dehghani
- Publisher
- Elsevier Science
- Year
- 1991
- Tongue
- French
- Weight
- 237 KB
- Volume
- 32
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
A stereocontrolled synthesis of (f)-pumiliotoxin C was achieved from I-methoxypyridine in seven steps.
📜 SIMILAR VOLUMES
## The mdohzrdme alkalords (+)-septlane and (k)-tylophonne were prepared from N-acyldLhydropyndone 7 tn five and SW steps, respectively Recently we hdve been studying the synthesis and synthetic utility of N-acyl-2,3-dlhydm-4-pyndoneq These highly functlonJlzed heterocycles are conveniently prepar
The trans-pip&dine alkaloid, (-)-solenopsin A. was prepared in seven steps from readily available 4-~haxy-3\_(niiropropyrsilyllpyrfdin in 43% overall yield. The addition of organ~tallics to chiral 1-acylpyridinium salt 1 gives N-acyl-2-alkyl-23&hydta~4pyridones 2 with high diastereoselectivity.\*~ T
Pumiliotoxin C (Q is one of a large group of structurally related toxins which have been isolated from shin extracts of the colorful Central American poison arrow frog Dendrobates pu milio 2, 3, 4, 5c . Synthetic investigations in several laboratories culminated in 1975 in three total syniheses of t