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

Kana Suzuki | Zendy; Yasunao Hattori | Zendy; Atsushi Kawamura | Zendy; Hidefumi Makabe | Zendy

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

Author(s) -

Kana Suzuki,

Yasunao Hattori,

Atsushi Kawamura,

Hidefumi Makabe

Publication year - 2021

Publication title -

bioscience biotechnology and biochemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.509

H-Index - 116

eISSN - 1347-6947

pISSN - 0916-8451

DOI - 10.1093/bbb/zbaa014

Subject(s) - piperidine , moiety , alkylation , catalysis , stereoselectivity , chemistry , double bond , palladium , ring (chemistry) , medicinal chemistry , stereochemistry , organic chemistry

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.

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