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Syntheses without protection: a three-step synthesis of optically active clavicipitic acid by utiliz

Syntheses without protection: a three-step synthesis of optically active clavicipitic acid by utiliz

  1. ThirdEyeFloond
    Tetrahedron Letters 40 (1999) 7803-7806

    Yuusaku Yokoyama, Hidemasa Hikawa, Masaharu Mitsuhashi, Aki Uyama and Yasuoki Murakami

    Abstract
    The optically active clavicipitic acid (4), an ergot alkaloid, was synthesized by a three-step sequence from 4-bromoindole (1). The reaction of 1 with d/-serinĀ¢ (2) in the presence of Ac20 followed by enzymatic kinetic resolution gave (S)-4-bromotryptophan (3). The Heck reaction of 3 with 1,1-dimethylallylalcohol in aqueous media gave clavicipitic acid in one-pot.