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.
Publication types
-
Research Support, N.I.H., Extramural
-
Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
-
Cyclization
-
Diketopiperazines / chemical synthesis*
-
Diketopiperazines / chemistry
-
Diketopiperazines / pharmacology
-
Drug Screening Assays, Antitumor
-
HeLa Cells
-
Humans
-
Indole Alkaloids / chemical synthesis*
-
Indole Alkaloids / chemistry
-
Indole Alkaloids / pharmacology
-
Indoles / chemical synthesis*
-
Indoles / chemistry
-
Indoles / pharmacology
-
Molecular Structure
-
Piperazines / chemical synthesis*
-
Piperazines / chemistry
-
Piperazines / pharmacology
-
Stereoisomerism
Substances
-
Diketopiperazines
-
Indole Alkaloids
-
Indoles
-
Piperazines
-
epipolythiodiketopiperazine
-
luteoalbusin A
-
luteoalbusin B
-
indole