Quebrachitol: a versatile building block in the construction of naturally occurring bioactive materials

Article Abstract:

The optically active cyclitol, L-quebrachitol (1-L-{-}-2-O-methyl-chiro- inositol, 1) is a chiral structural block for the preparation of biologically active compounds in enantiomerically pure form. The cyclic structure of 1 is utilized to obtain acyclic molecules and the 6-membered ring allows the arrangement of ring structures by expansion or contraction of the ring. 1 is the precursor for inositol phosphates, L-mannitol and a variety of antibiotics and enzyme inhibitors.

Analysis, Inositol phosphates

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Fluorinated ylides and related compounds

Article Abstract:

The reaction between fluorocarbons and triphenylphosphine under specific reaction conditions gives fluorinated ylides. Fluorinated ylides play an important role in the introduction of fluorine atoms, perfluoroalkyl or perfluorocycloalkyl groups into an organic compound. The mechanism involves the formation of a difluoro carbene in the transition state. The addition reaction of fluorinated ylides is highly regio- and stereo-specific.

Fluorine compounds

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Selective fluorinations by reagents containing the OF group

Article Abstract:

Electrophilic fluorination involves hypofluorite reagents like fluoroxytrifluoromethane, CF3OF. The process provides proof for Olah's three center-two electron nonclassical carbonium ion postulation for electrophilic reactions on sp3-hybridized carbon atom. A one electron transition generates the trifluoromethoxy radicals in the transition state. CF3OF also brings about aromatic fluorination in a regio- and stereo-selective manner.

Aromatic compounds, Fluorination

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