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Studies on synthesis of biologically active natural indole compounds and related compounts utilized asymmetric domino reactions

利用不对称多米诺反应合成具有生物活性的天然吲哚化合物及相关化合物的研究

基本信息

批准号：
14572018
负责人：
KAWASAKI Tomomi
金额：
$ 2.18万
依托单位：
MEIJI PHARMACEUTICAL UNIVERSITY
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
2002
资助国家：
日本
起止时间：
2002 至 2003
项目状态：
已结题

项目摘要

We recently developed the method for construction of asymmetric quarternary carbon center using stereoselective domino reactions, and now we have applied our method to asymmetric synthesis of biologically active pyrrolo[2,3-b]indoles, pseudophyrinaminol, flustramines, amauromin, and physostigumin derivatives. As its further application to construction of tertiary alcohol, we have approached to 3a-hydroxypyrrolo[2,3-b]indoles, flustraminol and alline.1.The tandem olefination, isomerization and Claisen rearrangement of 2-allyloxyindolin-3-ones, derived from optically active allyl alcohols, proceeded high-stereoselectively to give optically active 3,3-disubstituted oxindoles, which were reduced to give optically active 3a-allylpyrrolo[2,3-b]indoles. We have accomplished efficiently asymmetric total synthesis of pseudophyrinaminol and flustramines A and B.2.Olefination of 2-allylindolin-3-ones with optically active ylides, followed by isomerization to proceed asymmetric Claisen rearrangement to afford the optically active oxindoles in high yields. We have succeeded in total synthesis of unnatural pseudophyrinaminol.3.We have achieved synthesis of 3a-allylphenserin as physostigumin derivative having the bulky moiety at 3a position..4.We have established the synthetic method for 3-hydroxyoxindoles utilizing enolization-Claisen rearrangement of 2-allyloxyindolin-3-ones, and we have achieved total synthesis of donaxiridine, alline, and comvolutamydines A and B.

我们最近发展了利用立体选择性多米诺反应构建不对称季碳中心的方法，现在我们已经将我们的方法应用于具有生物活性的吡咯并[2，3-B]吲哚、假白藜芦醇、氟曲明、苦黑素和毒扁豆碱衍生物的不对称合成。1.由光学活性的烯丙醇衍生的2-烯丙氧基吲哚啉-3-酮经烯化、异构化和Claisen重排反应，高立体选择性地得到光学活性的3，3-二取代羟吲哚，再经还原得到光学活性的3a-烯丙基吡咯并[2，3-B]吲哚，3-B]吲哚。我们高效地完成了假白藜芦醇和氟斯特明A和B的不对称全合成。2. 2-烯丙基吲哚-3-酮与光学活性叶立德的烯化反应，然后异构化进行不对称克莱森重排，高产率地得到光学活性羟吲哚。3.合成了在3a位上具有大体积结构的毒扁豆素衍生物3a-烯丙基酚色林。4.建立了2-烯丙氧基吲哚啉-3-酮的烯醇化-Claisen重排反应合成3-羟基羟吲哚的方法，实现了donaxiridine、alline和comvolutamydines A和B的全合成。