ABSTRACT
The total syntheses of (+)-vigulariol and (-)-sclerophytin A are reported in 15 steps and 16 steps, respectively, from a known compound. The flexible, readily scalable synthetic strategy allows for rapid construction of a critical tricyclic intermediate and is demonstrated via the synthesis of these two marine natural products. A key reaction in this synthetic protocol is a combination Wittig/intramolecular Diels-Alder cycloaddition.
Subject(s)
Bridged-Ring Compounds/chemical synthesis , Diterpenes/chemical synthesis , Ethers, Cyclic/chemical synthesis , Furans/chemical synthesis , Bridged-Ring Compounds/chemistry , Diterpenes/chemistry , Ethers, Cyclic/chemistry , Furans/chemistry , Molecular Conformation , StereoisomerismABSTRACT
The total synthesis of the originally proposed structure of briarellin J is reported in 15 steps from a known compound and in 23 steps from readily available materials. Key reactions include an exo-selective intramolecular Diels-Alder and a substrate-controlled hydroboration. Discrepancies in the spectroscopic data of the synthetic and natural material led to a revision of the assigned structure.
