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Total synthesis of enantiopure phalarine via a stereospecific Pictet-Spengler reaction: traceless transfer of chirality from L-tryptophan.

ABSTRACT: An appropriately constructed 2-substituted derivative of l-tryptophan undergoes conversion to a prephalarine structure in a single step. The reaction occurs in a diastereoselective fashion, leading shortly thereafter to the naturally occurring version of the alkaloid phalarine.

SUBMITTER: Trzupek JD

PROVIDER: S-EPMC2895623 | biostudies-literature | 2010 Jun

REPOSITORIES: biostudies-literature

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Total synthesis of enantiopure phalarine via a stereospecific Pictet-Spengler reaction: traceless transfer of chirality from L-tryptophan.

Trzupek John D JD Lee Dongjoo D Crowley Brendan M BM Marathias Vasilios M VM Danishefsky Samuel J SJ

Journal of the American Chemical Society 20100601 24

An appropriately constructed 2-substituted derivative of l-tryptophan undergoes conversion to a prephalarine structure in a single step. The reaction occurs in a diastereoselective fashion, leading shortly thereafter to the naturally occurring version of the alkaloid phalarine. ...[more]

PMID: 20509657

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