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ChemInform Abstract: Total Syntheses of (.+-.)-Cryptopleurine, (.+-.)-Antofine, and (.+-.)-Deoxypergularinine.

✍ Scribed by Stephane Lebrun; Axel Couture; Eric Deniau; Pierre Grandclaudon


Publisher
John Wiley and Sons
Year
2010
Weight
34 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis


Total Syntheses of (Β±)-Cryptopleurine, (Β±)-Antofine, and (Β±)-Deoxypergularinine.

-Synthesis of cryptopleurine (X), antofine (VIIa), and deoxypergularinine (VIIb) emphasizes the synthetic potential of enecarbamates (III) and (IX). These key intermediates are of interest for the preparation of other naturally occurring phenanthroquinolizidine and -indolizidine alkaloids as well as their biogenetically related congeners. -(LEBRUN, STEPHANE;


πŸ“œ SIMILAR VOLUMES


Total syntheses of (Β±)-cryptopleurine, (
✍ StΓ©phane Lebrun; Axel Couture; Eric Deniau; Pierre Grandclaudon πŸ“‚ Article πŸ“… 1999 πŸ› Elsevier Science 🌐 French βš– 618 KB

The alkaloids (+)-cryptopleurine 1, (+)-antofine 2, and (+)-deoxypergularinine 3 were synthesized by Pictet-Spengler cyclization of the 2-arylmethylpiperidine and -pyrrolidines 4, 5 and 6 obtained by sequential N-deprotection-reduction of the parent enecarbamates 7, 8 and 9. These latter were made b