Stereospecific synthesis of 2,3,6-trisubstituted piperidines: an efficient total synthesis of (.+-.)-pumiliotoxin C
โ Scribed by LeBel, Norman A.; Balasubramanian, N.
- Book ID
- 126910938
- Publisher
- American Chemical Society
- Year
- 1989
- Tongue
- English
- Weight
- 809 KB
- Volume
- 111
- Category
- Article
- ISSN
- 0002-7863
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๐ SIMILAR VOLUMES
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
Reduction of the enantiopure b-amino esters 10 provides the g-amnio alcohol 11, which is condensed with 2,4-pentadione to afford 12. Stepwise cyclization of 12 produced the cyclic enamine 13, which is hydrogenated to deliver all cis-2,3,6-trisubstituted piperidine 14. Using this reaction sequence an