Optically Active Total Synthesis of Clavicipitic Acid
Optically Active Total Synthesis of Clavicipitic Acid
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DOI：
10.1021/jo00111a004
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发表时间：
1995-03
影响因子：
3.6
通讯作者：
Y. Yokoyama;Toshifumi Matsumoto;Y. Murakami
中科院分区：
文献类型：
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作者：
Y. Yokoyama;Toshifumi Matsumoto;Y. Murakami
由于 DMAT (3) 是由 L-色氨酸 (4) 生物合成的，因此市售的 L-色氨酸 (4) 可能是合成光学活性麦角生物碱的良好起始材料。然而，据报道只取得了有限的成功。 4 主要障碍是吲哚环对位的选择性取代。我们希望报告光学活性麦角二酸（la 和 lb）的首次全合成。 5 该合成采用 (S)-4-溴色氨酸 (5) 作为关键中间体，并通过 4-(T, T-二甲基-T-羟基-2-丙烯基-
Since DMAT (3) is biosynthesizedfrom L-tryptophan (4), commercially available L-tryptophan (4) might be a good starting material for the synthesis of optically active ergot alkaloids. Only limited success has been reported, however. 4 The chief obstacle has been the selective substitution at the Opposition of the indole ring. We wish to report the first total syntheses of the opticallyactive clavicipitic acids (la and lb). 5 The synthesis employs (S)-4-bromotryptophan (5) as a key intermediate and occurs via 4-(T, T-dimethyl-T-hydroxy-2-propenyl-