1.
Chem Commun (Camb)
; 49(6): 558-60, 2013 Jan 21.
Article
in English
| MEDLINE
| ID: mdl-23128288
ABSTRACT
The first synthesis of marinopyrrole B, which is highly active against methicillin-resistant Staphylococcus aureus, is described. The route involved constructing a pyrrole ring on the nitrogen of a 3-bromo-4,5-dichloropyrrole by N-alkylation with a special Michael acceptor having an allylic leaving group; the second pyrrole ring was then formed by a Paal-Knorr reaction.
Subject(s)
Anti-Bacterial Agents/chemical synthesis , Pyrroles/chemical synthesis , Alkylation , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Crystallography, X-Ray , Methicillin-Resistant Staphylococcus aureus/drug effects , Molecular Conformation , Pyrroles/chemistry , Pyrroles/pharmacology , Stereoisomerism
2.
J Org Chem
; 73(15): 6018-21, 2008 Aug 01.
Article
in English
| MEDLINE
| ID: mdl-18593186
ABSTRACT
Selenium-stabilized carbanions are available by a route that does not involve acid-catalyzed formation of selenoacetals. Aldehydes are converted first into alpha-hydroxystannanes and then into alpha-(phenylseleno)stannanes. Treatment with BuLi affords selenium-stabilized carbanions by preferential Sn/Li exchange.
