Stereoselective Synthesis of Baulamycin A.
J Org Chem
; 85(5): 3812-3823, 2020 03 06.
Article
em En
| MEDLINE
| ID: mdl-31970985
ABSTRACT
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.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Resorcinóis
/
Álcoois Graxos
Idioma:
En
Ano de publicação:
2020
Tipo de documento:
Article