Efficient construction of bioactive trans-5A5B6C spirolactones via bicyclo[4.3.0] α-hydroxy ketones

Y. J. Zhu; J. Q. Huo; Z. J. Fan; Q. F. Wu; X. Li; S. Zhou; L. X. Xiong; T. Kalinina; T. Glukhareva

doi:10.1039/C7OB02701J

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Efficient construction of bioactive trans-5_A5_B6_C spirolactones via bicyclo[4.3.0] α-hydroxy ketones†

Y. J. Zhu,

^a J. Q. Huo,^b Z. J. Fan,*^ac Q. F. Wu,^a X. Li,^a S. Zhou,^a L. X. Xiong,^a T. Kalinina^d and T. Glukhareva*^d

Author affiliations

* Corresponding authors

^a State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, P. R. China
E-mail: fanzj@nankai.edu.cn

^b College of Plant Protection, Agricultural University of Hebei, Baoding 071001, P. R. China

^c Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, P. R. China

^d The Ural Federal University Named after the First President of Russia B. N. Yeltsin, 19 Mira Str., Ekaterinburg 620002, Russia
E-mail: taniagluhareva@yandex.ru

Abstract

An efficient, convenient short synthetic procedure for the synthesis of the intricate 5_A5_B6_C-ring fusion topologies of tricyclic spiranoid β-hydroxybutyrolactones through lactonization of the key intermediate trans-α-hydroxyindenones with malonates is described. All the compounds synthesized exhibited environmentally benign characteristics, moderate fungicidal, nematocidal, and anti-TMV activities.

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Article information

DOI: https://doi.org/10.1039/C7OB02701J
Article type: Paper
Submitted: 03 Nov 2017
Accepted: 18 Jan 2018
First published: 18 Jan 2018

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Org. Biomol. Chem., 2018,16, 1163-1166

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Efficient construction of bioactive trans-5_A5_B6_C spirolactones via bicyclo[4.3.0] α-hydroxy ketones

Y. J. Zhu, J. Q. Huo, Z. J. Fan, Q. F. Wu, X. Li, S. Zhou, L. X. Xiong, T. Kalinina and T. Glukhareva, Org. Biomol. Chem., 2018, 16, 1163 DOI: 10.1039/C7OB02701J

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Organic & Biomolecular Chemistry