Open AccessA Concise Approach to Paxilline Indole Diterpenes
Author(s) -
David T. George,
Eric J. Kuenstner,
С. В. Пронин
Publication year - 2015
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.5b11129
Subject(s) - chemistry , stereocenter , indole test , regioselectivity , aldol reaction , tandem , indole alkaloid , vicinal , stereochemistry , cascade reaction , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis , materials science , composite material
A synthetic approach to paxilline indole diterpenes is described. The route to the pentacyclic core relies on a new regioselective alkenylation of ketones and a tandem radical addition-aldol reaction sequence to access vicinal quaternary stereocenters. Emindole SB, the simplest member of the family, is synthesized in 11 steps from commercially available material to demonstrate the application of this approach.