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Synthesis of 2-substituted tryptophans via a C3- to C2-alkyl migration.

ABSTRACT: The reaction of 3-substituted indoles with dehydroalanine (Dha) derivatives under Lewis acid-mediated conditions has been investigated. The formation of 2-substituted tryptophans is proposed to occur through a selective alkylative dearomatization-cyclization followed by C3- to C2-alkyl migration and rearomatization.

SUBMITTER: Mari M

PROVIDER: S-EPMC4168769 | biostudies-literature | 2014

REPOSITORIES: biostudies-literature

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Synthesis of 2-substituted tryptophans via a C3- to C2-alkyl migration.

Mari Michele M Lucarini Simone S Bartoccini Francesca F Piersanti Giovanni G Spadoni Gilberto G

Beilstein journal of organic chemistry 20140826

The reaction of 3-substituted indoles with dehydroalanine (Dha) derivatives under Lewis acid-mediated conditions has been investigated. The formation of 2-substituted tryptophans is proposed to occur through a selective alkylative dearomatization-cyclization followed by C3- to C2-alkyl migration and rearomatization. ...[more]

PMID: 25246958

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