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对映选择性和非对映选择性偶氮偶联/亚胺离子环化反应：(-)-psychotriasine和(+)-pestalazine B全合成的统一策略

Enantioselective and diastereoselective azo-coupling/iminium-cyclizations: a unified strategy for the total syntheses of (-)-psychotriasine and (+)-pestalazine B.

作者信息

Li Qi, Xia Tingting, Yao Licheng, Deng Haiteng, Liao Xuebin

机构信息

Tsinghua-Peking Centre for Life Sciences , Beijing 100084 , China.

Department of Pharmacology and Pharmaceutical Sciences , School of Medicine , Collaborative Innovation Center for Diagnosis and Treatment of Infectious Diseases , Tsinghua University , Beijing 100084 , China . Email:

出版信息

Chem Sci. 2015 Jun 1;6(6):3599-3605. doi: 10.1039/c5sc00338e. Epub 2015 May 5.

DOI:10.1039/c5sc00338e
PMID:29511522
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5659145/
Abstract

We report a unified strategy for the total syntheses of (-)-psychotriasine and (+)-pestalazine B based on the advanced intermediates of 3α-amino-hexahydropyrrolo[2,3-]indole. To construct these structural motifs, a cascade reaction involving a BINOL-derived phosphoric anion-paired catalyst for enantioselective or diastereoselective azo-coupling/iminium-cyclizations was developed. The remaining key steps of the synthesis involve a sterically hindered amination hypervalent iodine reagents and the Larock annulation. These transformations enable a general approach to the syntheses of indole alkaloids containing a 3α-amino-hexahydropyrrolo[2,3-]indole motif and could be further applied to build a natural product-based library.

摘要

我们报道了一种基于3α-氨基-六氢吡咯并[2,3 -]吲哚高级中间体的(-)-Psychotriasine和(+)-Pestalazine B的全合成统一策略。为构建这些结构基序，开发了一种涉及BINOL衍生的磷酸阴离子配对催化剂的级联反应，用于对映选择性或非对映选择性偶氮偶联/亚胺离子环化反应。合成的其余关键步骤包括位阻胺化、高价碘试剂和Larock环化反应。这些转化为含有3α-氨基-六氢吡咯并[2,3 -]吲哚基序的吲哚生物碱的合成提供了一种通用方法，并且可进一步应用于构建基于天然产物的文库。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8daf/5659145/8f73c9445c2a/c5sc00338e-s4.jpg
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