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Concise Total Synthesis of (+)-Luteoalbusins A and B.

ABSTRACT: The first total synthesis of (+)-luteoalbusins A and B is described. Highly regio- and diastereoselective chemical transformations in our syntheses include a Friedel-Crafts C3-indole addition to a cyclotryptophan-derived diketopiperazine, a late-stage diketopiperazine dihydroxylation, and a C11-sulfidation sequence, in addition to congener-specific polysulfane synthesis and cyclization to the corresponding epipolythiodiketopiperazine. We also report the cytoxicity of both alkaloids, and closely related derivatives, against A549, HeLa, HCT116, and MCF7 human cancer cell lines.

SUBMITTER: Adams TC

PROVIDER: S-EPMC4597594 | biostudies-literature | 2015 Sep

REPOSITORIES: biostudies-literature

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Concise Total Synthesis of (+)-Luteoalbusins A and B.

Adams Timothy C TC Payette Joshua N JN Cheah Jaime H JH Movassaghi Mohammad M

Organic letters 20150825 17

The first total synthesis of (+)-luteoalbusins A and B is described. Highly regio- and diastereoselective chemical transformations in our syntheses include a Friedel-Crafts C3-indole addition to a cyclotryptophan-derived diketopiperazine, a late-stage diketopiperazine dihydroxylation, and a C11-sulfidation sequence, in addition to congener-specific polysulfane synthesis and cyclization to the corresponding epipolythiodiketopiperazine. We also report the cytoxicity of both alkaloids, and closely ...[more]

PMID: 26336940

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