Tetrahedron Letters p. 7803 - 7806 (1999)
Update date:2022-07-30
Topics:
Yokoyama, Yuusaku
Hikawa, Hidemasa
Mitsuhashi, Masaharu
Uyama, Aki
Murakami, Yasuoki
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 dl-serine (2) in the presence of Ac2O 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.
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