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

Authors
  • Adams, Timothy C.
  • Payette, Joshua N.
  • Cheah, Jaime H.
  • Mo Movassaghi
Type
Published Article
Journal
Organic and Medicinal Chemistry Letters
Publisher
Springer (Biomed Central Ltd.)
Publication Date
Sep 13, 2015
Volume
17
Issue
17
Pages
17–4268
Identifiers
DOI: 10.1021/acs.orglett.5b02059
PMID: 26336940
PMCID: PMC4597594
Source
CCHF
License
Green

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.

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