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Studies in the aza-Cope reaction: a formal highly enantioselective synthesis of tryprostatin B

✍ Scribed by A Sofia Cardoso; Ana M Lobo; Sundaresan Prabhakar *

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 111 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)00455-x

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✦ Synopsis

The BF 3 -Et 2 O induced rearrangement of N-phthaloyl-1-(3,3-dimethylallyl)-L-tryptophane methyl ester proceeds without significant loss of its optical integrity to provide its 2-(3,3-dimethylallyl) isomer, a key intermediate in the synthesis of tryprostatin B.

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