Total synthesis of (+)-mupirocin H from D-glucose.
J Org Chem
; 76(15): 6331-7, 2011 Aug 05.
Article
em En
| MEDLINE
| ID: mdl-21707103
ABSTRACT
Enantioselective total synthesis of mupirocin H is accomplished starting from D-glucose featuring strategic application of D-glucose derived chirality, diastereoselective Still-Barrish hydroboration, and further elaboration of carbon chain to furnish a phenyltetrazolyl sulfone intermediate, which on coupling with (2S,3S)-2-methyl-3-(triisopropylsilyloxy)butanal under Julia-Kocienski olefination conditions gave an advanced E-olefinic intermediate selectively. The E-olefin was transformed to the 4-hydroxynitrile, a prefinal substrate, which on acid-catalyzed oxidative lactonization furnished the target molecule mupirocin H in 19 steps from known compound 6 (longest linear sequence) with an overall yield of 4.96%.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Mupirocina
/
Alcenos
/
Glucose
Idioma:
En
Ano de publicação:
2011
Tipo de documento:
Article