ABSTRACT
Two transannular (TA) aldol reactions were used to assemble the tricyclic carbon skeleton found in the tigliane and daphnane classes of diterpene natural products.
Subject(s)
Biological Products/chemistry , Biological Products/chemical synthesis , Diterpenes/chemistry , Diterpenes/chemical synthesisABSTRACT
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.
Subject(s)
Acetylcysteine/analogs & derivatives , Lactones/chemical synthesis , Acetylcysteine/chemical synthesis , Acetylcysteine/chemistry , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Crystallography, X-Ray , Lactones/chemistry , StereoisomerismABSTRACT
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.
