Synthesis of (+)-solenopsin via Pd-catalyzed N-alkylation and cyclization-Reference-Cited by-同舟云学术

Synthesis of (+)-solenopsin via Pd-catalyzed N-alkylation and cyclization

Published:2021-01-20 Issue:2 Volume:85 Page:223-227
ISSN:1347-6947
Container-title:Bioscience, Biotechnology, and Biochemistry
language:en
Short-container-title:

Author:

Suzuki Kana¹,Hattori Yasunao²,Kawamura Atsushi³,Makabe Hidefumi¹³

Affiliation:

1. Graduate School of Science and Technology, Department of Agriculture, Division of Food Science and Biotechnology, Shinshu University, Kami-ina, Nagano, Japan

2. Center for Instrumental Analysis, Kyoto Pharmaceutical University, Yamashina-ku, Kyoto, Japan

3. Department of Biomolecular Innovation, Institute for Biomedical Sciences, Interdisciplinary Cluster for Cutting Edge Research, Shinshu University, Kami-ina, Nagano, Japan

Abstract

ABSTRACT Synthesis of (+)-solenopsin, a 2,6-disubstituted piperidine alkaloid, isolated from fire ants (Solenopsis), was achieved. Stereoselective construction of trans-2,6-piperidine ring moiety was performed using palladium-catalyzed cyclization. Chain elongation using Grubbs 2nd catalyst followed by the reduction of double bond and the deprotection of the Cbz group afforded (+)-solenopsin.

Funder

JSPS

Publisher

Oxford University Press (OUP)

Subject

Organic Chemistry,Molecular Biology,Applied Microbiology and Biotechnology,General Medicine,Biochemistry,Analytical Chemistry,Biotechnology

Link

http://academic.oup.com/bbb/article-pdf/85/2/223/36666916/zbaa014.pdf

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