Stereoselective synthesis of a Podophyllum lignan core by intramolecular reductive nickel-catalysis

Jian Xiao; Xiao-Wei Cong; Gui-Zhen Yang; Ya-Wen Wang; Yu Peng

doi:10.1039/C8CC00001H

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Stereoselective synthesis of a Podophyllum lignan core by intramolecular reductive nickel-catalysis†

Jian Xiao,^a Xiao-Wei Cong,^a Gui-Zhen Yang,^a Ya-Wen Wang^ab and Yu Peng

*^ab

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* Corresponding authors

^a State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China
E-mail: pengyu@lzu.edu.cn

^b School of Life Science and Engineering, Southwest Jiaotong University, Chengdu, China

Abstract

A Ni-catalyzed reductive cascade to a diastereocontrolled construction of THN[2,3-c]furan, is developed. The mild reaction conditions led to the tolerance of broad functional groups that can be placed in almost every position of this skeleton with good yields. The conformational control for the observed trans- or cis-fused selectivity during this tandem cyclization-coupling is also proposed.

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DOI: https://doi.org/10.1039/C8CC00001H
Article type: Communication
Submitted: 01 Jan 2018
Accepted: 29 Jan 2018
First published: 07 Feb 2018

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Chem. Commun., 2018,54, 2040-2043

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Stereoselective synthesis of a Podophyllum lignan core by intramolecular reductive nickel-catalysis

J. Xiao, X. Cong, G. Yang, Y. Wang and Y. Peng, Chem. Commun., 2018, 54, 2040 DOI: 10.1039/C8CC00001H

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Chemical Communications

Stereoselective synthesis of a Podophyllum lignan core by intramolecular reductive nickel-catalysis†

Abstract

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Stereoselective synthesis of a Podophyllum lignan core by intramolecular reductive nickel-catalysis

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