Concise Total Synthesis of (+)-Luteoalbusins A and B
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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.
Date issued
2015-09Department
Massachusetts Institute of Technology. Department of Chemistry; Koch Institute for Integrative Cancer Research at MITJournal
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
ISSN
1523-7060
1523-7052