ABSTRACT
A unique photochemical flow reactor featuring quartz tubing, an aluminum mirror and temperature control has been developed for the photo-induced electron-transfer deoxygenation reaction to produce 2'-deoxy and 2',3'-dideoxynucleosides. The continuous flow format significantly increased the efficiency and selectivity of the reaction.
Subject(s)
Carbazoles/chemistry , Chemistry Techniques, Synthetic/instrumentation , Dideoxynucleosides/chemical synthesis , Photosensitizing Agents/chemistry , Aluminum/chemistry , Carbazoles/chemical synthesis , Catalysis , Chemistry Techniques, Synthetic/economics , Dideoxynucleosides/chemistry , Equipment Design , Photosensitizing Agents/chemical synthesis , Time Factors , Ultraviolet RaysABSTRACT
[reaction: see text] An asymmetric synthesis of the heavily oxygenated inner sector of amphidinol 3 constituted of C31-C52 is described. The successful pathway highlights construction of the pair of identical tetrahydropyran subunits from a common intermediate.
Subject(s)
Alkenes/chemical synthesis , Antifungal Agents/chemical synthesis , Dinoflagellida/chemistry , Pyrans/chemical synthesis , Aldehydes/chemistry , Alkenes/pharmacology , Animals , Antifungal Agents/pharmacology , Epoxy Compounds/chemistry , Hydrocarbons, Iodinated/chemistry , Models, Chemical , Oxygen/chemistry , Pyrans/chemistry , Pyrans/pharmacology , Stereoisomerism , Vinyl Compounds/chemistryABSTRACT
[reaction: see text] The ability of methyl(trifluoromethyl)dioxirane to cleave p-methoxylbenzyl ethers oxidatively in the presence of various additional functional groups has been investigated. These reactions, performed in aqueous acetonitrile, transform a reasonably robust aryl substituent into a dienyl aldehydo ester. The originally generated E,Z-isomer undergoes slow conversion to the more stable E,E-form at 20 degrees C.
