State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engeneering, Lanzhou University , Lanzhou 730000, China.
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
Org Lett. 2016 Aug 19;18(16):4076-9. doi: 10.1021/acs.orglett.6b01968. Epub 2016 Aug 4.
A Rh(II)-catalyzed dearomative intramolecular [3 + 2] dipolar cycloaddition involving the indolic C2-C3 carbon-carbon double bond has been developed. The reaction was launched from the triazole moiety within the substrate and proceeded efficiently under mild conditions. A wide range of functional groups could be tolerated. These features render the current reaction a highly useful tool for the synthesis of polycyclic indole alkaloids, as showcased by a rapid assembly of the core structure of Aspidosperma and the related alkaloids.
一种 Rh(II)催化的涉及吲哚 C2-C3 碳-碳双键的去芳构化分子内[3+2]偶极环加成反应已经被开发出来。该反应从底物中的三唑部分引发，并在温和条件下高效进行。广泛的官能团可以被容忍。这些特点使得当前的反应成为多环吲哚生物碱合成的非常有用的工具，如 Aspidosperma 及其相关生物碱的核心结构的快速组装所示。
