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. 2015 Sep 4;17(17):4268-71.
doi: 10.1021/acs.orglett.5b02059. Epub 2015 Aug 25.

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

Timothy C Adams  1 , Joshua N Payette  1 , Jaime H Cheah  2 , Mohammad Movassaghi  1
Affiliations

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

Timothy C Adams et al. Org Lett. .

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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Figures

Figure 1
Figure 1
Representative ETP Alkaloids
Scheme 1
Scheme 1
Retrosynthetic Analysis
Scheme 2
Scheme 2
Preparation of Key Intermediate (+)-11
Scheme 3
Scheme 3
Synthesis of (+)-Luteoalbusin A (1) and B (2)
See this image and copyright information in PMC

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