RESUMEN
Two transannular (TA) aldol reactions were used to assemble the tricyclic carbon skeleton found in the tigliane and daphnane classes of diterpene natural products.
Asunto(s)
Productos Biológicos/química , Productos Biológicos/síntesis química , Diterpenos/química , Diterpenos/síntesis químicaRESUMEN
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
An alkylidene carbene 1,5-CH insertion has been used as a key step in an efficient enantioselective total synthesis of (-)-clasto-lactacystin beta-lactone, and its C7-epimer. 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.