RESUMEN
An alkylidene carbene 1,5-CH insertion has been used as a key step in an enantioselective total syntheses of omuralide, its C7-epimer, and (+)-lactacystin. An additional noteworthy feature of the synthesis is the use of a novel oxidative deprotection procedure, utilizing DMDO, for the conversion of a late-stage benzylidene acetal into a primary alcohol and a secondary benzoate ester.
Asunto(s)
Acetilcisteína/análogos & derivados , Lactonas/síntesis química , Acetilcisteína/síntesis química , Acetilcisteína/química , Antibacterianos/síntesis química , Antibacterianos/química , Cristalografía por Rayos X , Lactonas/química , EstereoisomerismoRESUMEN
The enantioselective synthesis of acyclic pyrrole, indole and other N-carbazole carbinols via ligand-mediated addition of lithium carbazolates to aldehydes, together with studies into their catalytic enantioselective synthesis using substoichiometric base and ligand, are reported. The subsequent exploitation of the resulting stereocentre as a controlling element in 1,3-syn- and anti-selective reduction of beta-ketones and elaboration to homoallylic alcohols is also described.