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Total syntheses of (±)-cryptopleurine, (±)-antofine and (±)-deoxypergularinine

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

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 618 KB
Volume: 55
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(99)00017-4

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✦ Synopsis

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 by the Homer reaction of phosphorylated carbamates 12 and 13 with the appropriate aldehydes 10 and 11.

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