RESUMO
Two transannular (TA) aldol reactions were used to assemble the tricyclic carbon skeleton found in the tigliane and daphnane classes of diterpene natural products.
Assuntos
Produtos Biológicos/química , Produtos Biológicos/síntese química , Diterpenos/química , Diterpenos/síntese químicaRESUMO
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.
Assuntos
Acetilcisteína/análogos & derivados , Lactonas/síntese química , Acetilcisteína/síntese química , Acetilcisteína/química , Antibacterianos/síntese química , Antibacterianos/química , Cristalografia por Raios X , Lactonas/química , EstereoisomerismoRESUMO
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.
