通过硫脲催化的双氧化吲哚的连续迈克尔反应全合成（+）-和（-）-卡利坎辛。
Total Synthesis of (+)- and (-)-Calycanthine by Means of Thio-Urea-Catalyzed Sequential Michael Reactions of Bis-oxindoles.
作者信息
Khatua Arindam, Jana Debgopal, Nandy Monosij, Shyamal Pranay, Bisai Alakesh
机构信息
Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal Bypass Road, Bhauri, Bhopal 462 066, Madhya Pradesh, India.
Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, Kalyani, Nadia 741 246, West Bengal, India.
出版信息
J Org Chem. 2024 Apr 5;89(7):4792-4801. doi: 10.1021/acs.joc.4c00019. Epub 2024 Mar 28.
A unified catalytic asymmetric approach to naturally occurring piperidinoindoline and pyrrololidinoindoline alkaloids has been realized via the development of a thio-urea-catalyzed sequential Michael addition of bis-oxindole onto nitroethylene (up to 93% ee and >20:1 dr). This strategy offers the total syntheses of either enantiomers of naturally occurring calycanthine.
通过开发一种硫脲催化的双氧化吲哚与硝基乙烯的连续迈克尔加成反应（对映体过量高达93%，非对映选择性大于20:1），实现了对天然存在的哌啶并吲哚啉和吡咯烷并吲哚啉生物碱的统一催化不对称合成方法。该策略实现了天然产物卡利坎辛两种对映体的全合成。
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