ABSTRACT
In this study, the total synthesis of 3-epi-juruenolide C is achieved in 10 steps (longest linear sequence) starting from ethyl (2E,4S,5S)-4,5-dihydroxy-2-hexenoate. The synthetic highlights of our approach include one-pot regioselective bromination, intramolecular carbonylation using bis(triphenylphosphine)dicarbonylnickel, and face-selective hydrogenation using a homogeneous Wilkinson's catalyst.
Subject(s)
Dioxoles/chemical synthesis , Lactones/chemical synthesis , Catalysis , Coordination Complexes/chemistry , Dioxoles/chemistry , Halogenation , Hydrogenation , Lactones/chemistry , Nickel/chemistry , Organophosphorus Compounds/chemistry , StereoisomerismABSTRACT
The first total syntheses of 3- epi-litsenolide D2 and its enantiomer lincomolide A were achieved. The synthetic highlights of our approach include olefin cross metathesis and bromine addition to the generated double bond, followed by the regioselective HBr-elimination and intramolecular carbonylation using bis(triphenylphosphine)dicarbonylnickel. This investigation also revealed that the previously reported specific optical rotation of 3- epi-litsenolide D2 should be revised.
