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Peng Y, Xiao J, Xu XB, et al. Stereospecific Synthesis of Tetrahydronaphtho[2,3-b]furans Enabled by a Nickel-Promoted Tandem Reductive Cyclization. Org Lett. 2016;18(19):5170-5173doi: 10.1021/acs.orglett.6b02665.
Peng, Y., Xiao, J., Xu, X. B., Duan, S. M., Ren, L., Shao, Y. L., & Wang, Y. W. (2016). Stereospecific Synthesis of Tetrahydronaphtho[2,3-b]furans Enabled by a Nickel-Promoted Tandem Reductive Cyclization. Organic letters, 18(19), 5170-5173. https://doi.org/10.1021/acs.orglett.6b02665
Peng, Yu, et al. "Stereospecific Synthesis of Tetrahydronaphtho[2,3-b]furans Enabled by a Nickel-Promoted Tandem Reductive Cyclization." Organic letters vol. 18,19 (2016): 5170-5173. doi: https://doi.org/10.1021/acs.orglett.6b02665
Peng Y, Xiao J, Xu XB, Duan SM, Ren L, Shao YL, Wang YW. Stereospecific Synthesis of Tetrahydronaphtho[2,3-b]furans Enabled by a Nickel-Promoted Tandem Reductive Cyclization. Org Lett. 2016 Oct 07;18(19):5170-5173. doi: 10.1021/acs.orglett.6b02665. Epub 2016 Sep 23. PMID: 27658859.
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Org Lett. 2016 Oct 07;18(19):5170-5173. doi: 10.1021/acs.orglett.6b02665. Epub 2016 Sep 23.

Stereospecific Synthesis of Tetrahydronaphtho[2,3-b]furans Enabled by a Nickel-Promoted Tandem Reductive Cyclization.

Organic letters

Yu Peng, Jian Xiao, Xiao-Bo Xu, Shu-Ming Duan, Li Ren, Yong-Liang Shao, Ya-Wen Wang

Affiliations

  1. State Key Laboratory of Applied Organic Chemistry, Lanzhou University , Lanzhou, Gansu 730000, China.

PMID: 27658859 DOI: 10.1021/acs.orglett.6b02665

Abstract

A Ni-mediated cascade to a stereoselective synthesis of trans-tetrahydronaphtho[2,3-b]furans is efficiently achieved for the first time. The mild reductive system can be easily generated from inexpensive and air-stable materials and shows a broad positional tolerance of substituents that were previously difficult or impossible to access by other methods. Facile syntheses toward new analogues of therapeutic agents (iso)deoxypodophyllotoxin are also reported. In addition, the inherent substrate control is disclosed for the observed unique stereoselectivities during cyclizations.

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