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

被引：0

作者：

Suzuki, Kana ^{[1
]}

Hattori, Yasunao ^{[2
]}

Kawamura, Atsushi ^{[3
]}

Makabe, Hidefumi ^{[1
,3
]}

机构：

[1] Shinshu Univ, Grad Sch Sci & Technol, Dept Agr, Div Food Sci & Biotechnol, Kami Ina, Nagano, Japan

[2] Kyoto Pharmaceut Univ, Ctr Instrumental Anal, Yamashina Ku, Kyoto, Japan

[3] Shinshu Univ, Inst Biomed Sci, Dept Biomol Innovat, Kami Ina, Nagano, Japan

来源：

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY | 2021年 / 85卷 / 02期

关键词：

natural product; piperidine alkaloid; palladium-catalyzed cyclization; fire ants; solenopsin; FIRE ANT VENOM; ALKALOIDS;

D O I：

10.1093/bbb/zbaa014

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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.

引用

页码：223 / 227

页数：5

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