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