Photolysis of alkoxy-substituted-I -alkenyl benrotriazoles provides a new route to spiro-oxindoles which has been utilised in a total synthesis of gelsemine.

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The synthesis of the amides 2 which are designed to be selectors containing the chiral N-(3,5-dinitrobenzoyl)cx-phenylglycine covalently linked to tetrabenzo[a,c,g,i]fluorene is described. These amides are strongly adsorbed onto porous graphitised carbon, which affords chiral stationary phases that are able to resolve both racemic aromatic alcohols 3 and the methyl esters of Fmoc amino acids 4 on microgram quantities using highpressure liquid chromatography. Two methods of preparation of these chiral phases from 2 and porous graphitised carbon are described and the stability of these phases to the chromatographic conditions and to water have also been investigated.Paper 5/02808F

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