Asymmetric aminohydroxylation of vinyl indoles: a short enantioselective synthesis of the bisindole alkaloids dihydrohamacanthin A and dragmacidin A
Asymmetric aminohydroxylation of vinyl indoles: a short enantioselective synthesis of the bisindole alkaloids dihydrohamacanthin A and dragmacidin A
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DOI：
10.1016/s0957-4166(02)00111-8
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发表时间：
2002-03-22
影响因子：
--
通讯作者：
Jiang, B
中科院分区：
文献类型：
--
作者：
Yang, CG;Wang, J;Jiang, B
本文描述了一种利用Sharpless不对称氨基羟基化反应从乙烯基吲哚直接对映选择性合成(S)- n -boc保护的α -吲哚-3-酰基甘氨酸的有效方法，其对映选择性高达94%，分离收率高达65%。以相应的n - boc保护的α -6-溴吲哚-3-酰基甘氨酸为关键中间体，实现了哈马黄素A和dragmacidin A的快速对映选择性合成。此外，通过非天然对映体的对映选择性全合成，确定了顺式和反式二氢哈马卡纳素A的绝对立体化学性质。(C) 2002 Elsevier Science Ltd.版权所有。
A useful approach for the direct enantioselective synthesis of (S)-N-boc-protected alpha-indol-3-ylglycinols from vinyl indoles using the Sharpless asymmetric aminohydroxylation reaction, with enantioselectivities of up to 94% and isolated yields of up to 65%, is described. Expeditious enantioselective syntheses of hamacanthin A and dragmacidin A have been achieved using the corresponding N-Boc-protected alpha-6-bromo-indol-3-ylglycinol as the key intermediate. Furthermore, the absolute stereochemistry of cis- and trans-dihydrohamacanthin A has been determined through the enantioselective total synthesis of the unnatural enantiomers. (C) 2002 Elsevier Science Ltd. All rights reserved.