Open AccessStereoselective Synthesis of Baulamycin A
Author(s) -
Jonathan R. Thielman,
David H. Sherman,
Robert M. Williams
Publication year - 2020
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.9b03443
Subject(s) - stereocenter , total synthesis , stereoselectivity , ozonolysis , natural product , chemistry , conjugate , combinatorial chemistry , stereochemistry , antibiotics , broad spectrum , enantioselective synthesis , catalysis , organic chemistry , biochemistry , mathematics , mathematical analysis
New structural classes of antibiotics are rare, structurally novel broad-spectrum antibiotics exceptionally so. The recently discovered baulamycins constitute a remarkable example of these highly prized compounds and, as such, have attracted considerable attention in the form of both synthetic efforts and biological studies. For the first time, we report a gram-scale preparation of the common carbon framework of the baulamycin family, as well as the total synthesis of its most potent member, baulamycin A. Our approach employs highly stereoselective, catalyst-controlled asymmetric conjugate additions to thioesters to set key stereocenters, as well as the first reported use of "dry ozonolysis" to reveal a masked carboxylic acid in the total synthesis of a natural product.