Kainic acid, isolated from the algae Digenea simplex1 and Centrocerus clavulatum,2 has been shown to possess constitution and relative configuration 1 (Scheme I) on the basis of chemical3 and X-ray evidence.4 Correlation of 1 with the structurally related seaweed constituents -allokainic acid5 (2) and domoic acid (3)6 indicated the identity of their C(2) configuration. However, the assignment of the depicted (25) configuration by means of Lutz's rule7 may be regarded as merely tentative.8•21 In view of the potent neuronal excitatory activity of kainic acid (1) and of domoic acid (3),9 we aimed at an enantioselective synthesis of 1 which fur-

Derivatives of the benzylamine antimycotics with an extra phenyl ring incorporated in the side chain have been prepared and their antifungal activity evaluated. The potency is strongly dependent on the distance between the two phenyl groups and the type of spacer. Linking the aryl rings with a quaternary carbon atom resulted in the identification of highly active compounds 7f and 12a, having a novel 4-benzylbenzylamine side chain. Compound 7f and its 7-benzo[b]thienyl analogue 12a show significantly enhanced efficacy, in particular against Candida albicans, and are among the most potent allyl/benzylamine antimycotics identified so far. Extended investigations with the benzylbenzylamine derivative 7f revealed that, in addition to the enhanced antimycotic profile, the compound is the first representative of the benzylamine antimycotics suitable for systemic treatment.

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