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Elaboration of 1-benzoyltetrahydroisoquinoline derivatives employing a Pictet–Spengler cyclization with α-chloro-α-phenylthioketones. Synthesis of O-methylvelucryptine

✍ Scribed by Claudio C Silveira; Carmem R Bernardi; Antonio L Braga; Teodoro S Kaufman

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 94 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)01998-0

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✦ Synopsis

The reaction of N-tosyl-b-phenethylamines with a-chloro-a-phenylthioketones, leading to 1-benzoyl-and 1-pivaloyl-tetrahydroisoquinolines under modified Pictet-Spengler conditions, is described. The synthesis of O-methylvelucryptine employing this transformation as a key step is reported.

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