Synthesis 2017; 49(16): 3576-3581
DOI: 10.1055/s-0036-1588804
special topic
© Georg Thieme Verlag Stuttgart · New York

Nickel-Promoted Reductive Cyclization Cascade: A Short Synthesis of a New Aromatic Strigolactone Analogue

Jian Xiao
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, P. R. of China   Email: pengyu@lzu.edu.cn
,
Ya-Wen Wang
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, P. R. of China   Email: pengyu@lzu.edu.cn
,
Yu Peng  *
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, P. R. of China   Email: pengyu@lzu.edu.cn
› Author Affiliations
Supported by: This work was supported by the National Natural Science Foundation of China (21472075) and the Ministry of Education of China (PCSIRT-15R28, lzujbky-2016-51, lzujbky-2016-ct02).
Further Information

Publication History

Received: 13 March 2017

Accepted after revision: 29 March 2017

Publication Date:
04 May 2017 (eFirst)

Published as part of the Special Topic Advanced Strategies in Synthesis with Nickel

Abstract

A stereospecific synthesis of the tetrahydro-2H-indeno[1,2-b]furan skeleton, which is embedded in bioactive aromatic strigolactones such as GR24, is realized by a nickel-mediated tandem cross-coupling for the first time. The observed cis-stereoselectivity during the intramolecular formation of the Csp3–Csp2 bond is rationalized through conformation analysis and DFT calculations.

Supporting Information

 
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