Concise Total Synthesis of (+)-Luteoalbusins A and B
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Concise total.pdf
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1.45 MB
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Author(s)
Adams, Timothy Cho
Payette, Joshua N.
Cheah, Jaime H
Movassaghi, Mohammad
Date Issued
September 2015
Journal
Organic Letters
Publisher
American Chemical Society (ACS)
Citation
Adams, Timothy C. et al. “Concise Total Synthesis of (+)-Luteoalbusins A and B.” Organic Letters 17.17 (2015): 4268–4271.
Version
Author's final manuscript
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Koch Institute for Integrative Cancer Research at MIT
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Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
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DOI of Published Version
https://doi.org/10.1021/acs.orglett.5b02059
