ABSTRACT
The stereoselective synthesis of two naturally occurring bioactive spiroacetals, aculeatins A and B has been accomplished using 1-tetradecanal as the starting material. The sequence introduces diastereoselective iodine-induced electrophilic cyclization and ring opening of epoxide with 1,3-dithiane as the key steps.
Subject(s)
Alkanes/chemical synthesis , Cyclohexanones/chemical synthesis , Spiro Compounds/chemical synthesis , Cyclization , StereoisomerismABSTRACT
A practical stereoselective synthesis of (6S)-5,6,dihydro-6-[(2R)-2-hydroxy-6-phenyl hexyl]-2H-pyran-2-one, a potent natural antifungal compound, is described. The sequence involves diastereoselective iodine-induced electrophilic cyclization, epoxide ring opening with a vinyl Grignard reagent and ring closing metathesis (RCM) as the key steps.
Subject(s)
Antifungal Agents/chemical synthesis , Epoxy Compounds/chemical synthesis , Structure-Activity Relationship , Antifungal Agents/pharmacology , Candidiasis/drug therapy , Catalysis , Cyclization , Drug Design , Epoxy Compounds/chemistry , Epoxy Compounds/pharmacology , Kinetics , Molecular Structure , Stereoisomerism , Tubulin Modulators/chemical synthesis , Tubulin Modulators/chemistryABSTRACT
Silica supported phosphomolybdic acid, an eco-friendly heterogeneous catalyst, has been found to be highly efficient for Friedlander synthesis of quinolines in excellent yields. A variety of ketones afford the quinolines smoothly. The catalyst can be easily recovered and reused.
