Total Synthesis without Protection: Three??Step Synthesis of Optically Active Clavicipitic Acids by a Biomimetic Route

Y Yokoyama, H Hikawa, M Mitsuhashi…

Index: Yokoyama, Yuusaku; Hikawa, Hidemasa; Mitsuhashi, Masaharu; Uyama, Aki; Hiroki, Yasuhiro; Murakami, Yasuoki European Journal of Organic Chemistry, 2004 ,  # 6  p. 1244 - 1253

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Citation Number: 34

Abstract

Abstract A three-step synthesis of a mixture of optically active cis-and trans-clavicipitic acids 6, which are ergot alkaloids, was achieved, starting from 4-bromoindole (7) and dl-serine (dl- 2). This short synthesis was made possible by omitting the protection and deprotection steps from the synthetic route. The key step was the spontaneous cyclization of 4-vinyltryptophan (10) formed from the Heck reaction of 4-bromotryptophan (8) with 2-methyl-3-buten-2-ol (9 ...