ol5b02059_si_001.pdf (3.69 MB)
Concise Total Synthesis of (+)-Luteoalbusins A and B
journal contribution
posted on 2015-09-04, 00:00 authored by Timothy
C. Adams, Joshua N. Payette, Jaime
H. Cheah, Mohammad MovassaghiThe 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.