Total synthesis of (-)-physovenine from (-)-3a-hydroxyfuroindoline

Total synthesis of (-)-physovenine from (-)-3a-hydroxyfuroindoline
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DOI:
10.1016/j.tetlet.2005.01.016
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发表时间:
2005-02-28
影响因子:
1.8
通讯作者:
Omura, S
Omura, S
中科院分区:
化学4区
文献类型:
--
作者:
Sunazuka, T;Yoshida, K;Omura, S

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以光学活性的(-)-3a-羟基呋喃吲哚(-)-2为起始原料,通过色酚1的改进的夏普莱斯环氧化反应合成了卡拉巴豆生物碱(-)-黄藤碱(-)-3。我们的策略包括立体定向的自由基取代反应和C5位的区域选择性氧化。(C)2005爱思唯尔有限公司。保留所有权利。
Total synthesis of calabar bean alkaloid (-)-physovenine (-)-3 has been achieved in a concise manner starting from optically active (-)-3a-hydroxyfuroindoline (-)-2, synthesized via modified Sharpless epoxidation of tryptophol 1. Our strategy involved a stereospecific radical substitution reaction and regioselective oxidation at the C5 position. (C) 2005 Elsevier Ltd. All rights reserved.