Divergent synthesis of 2,6-disubstituted piperidine alkaloid, (+)-spectaline by palladium-catalyzed cyclization

Masatomo Katsuyama; Masahiro Furuta; Kazuya Kobayashi; Kenta Teruya; Hidefumi Makabe; Kenichi Akaji; Yasunao Hattori

doi:10.3987/COM-15-13172

Divergent synthesis of 2,6-disubstituted piperidine alkaloid, (+)-spectaline by palladium-catalyzed cyclization

Masatomo Katsuyama, Masahiro Furuta, Kazuya Kobayashi, Kenta Teruya, Hidefumi Makabe, Kenichi Akaji, Yasunao Hattori

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

Convergent synthesis of 2,6-disubstituted piperidine alkaloid, (+)-spectaline is described. Using substrate-controlled diastereo-selective Pd(II)-catalyzed cyclization, both cis-2,6- and trans-2,6-disubstituted piperidine backbones were constructed from adequately protected precursors with high selectivity. Synthesis of (+)-spectaline containing cis-2,6-disubstituents was accomplished by 10 step reactions with a 31% total yield.

Original language	English
Pages (from-to)	959-969
Number of pages	11
Journal	Heterocycles
Volume	91
Issue number	5
DOIs	https://doi.org/10.3987/COM-15-13172
Publication status	Published - 2015
Externally published	Yes

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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title = "Divergent synthesis of 2,6-disubstituted piperidine alkaloid, (+)-spectaline by palladium-catalyzed cyclization",

abstract = "Convergent synthesis of 2,6-disubstituted piperidine alkaloid, (+)-spectaline is described. Using substrate-controlled diastereo-selective Pd(II)-catalyzed cyclization, both cis-2,6- and trans-2,6-disubstituted piperidine backbones were constructed from adequately protected precursors with high selectivity. Synthesis of (+)-spectaline containing cis-2,6-disubstituents was accomplished by 10 step reactions with a 31% total yield.",

author = "Masatomo Katsuyama and Masahiro Furuta and Kazuya Kobayashi and Kenta Teruya and Hidefumi Makabe and Kenichi Akaji and Yasunao Hattori",

note = "Publisher Copyright: {\textcopyright} 2015 The Japan Institute of Heterocyclic Chemistry.",

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doi = "10.3987/COM-15-13172",

language = "English",

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T1 - Divergent synthesis of 2,6-disubstituted piperidine alkaloid, (+)-spectaline by palladium-catalyzed cyclization

AU - Katsuyama, Masatomo

AU - Furuta, Masahiro

AU - Kobayashi, Kazuya

AU - Teruya, Kenta

AU - Makabe, Hidefumi

AU - Akaji, Kenichi

AU - Hattori, Yasunao

PY - 2015

Y1 - 2015

N2 - Convergent synthesis of 2,6-disubstituted piperidine alkaloid, (+)-spectaline is described. Using substrate-controlled diastereo-selective Pd(II)-catalyzed cyclization, both cis-2,6- and trans-2,6-disubstituted piperidine backbones were constructed from adequately protected precursors with high selectivity. Synthesis of (+)-spectaline containing cis-2,6-disubstituents was accomplished by 10 step reactions with a 31% total yield.

AB - Convergent synthesis of 2,6-disubstituted piperidine alkaloid, (+)-spectaline is described. Using substrate-controlled diastereo-selective Pd(II)-catalyzed cyclization, both cis-2,6- and trans-2,6-disubstituted piperidine backbones were constructed from adequately protected precursors with high selectivity. Synthesis of (+)-spectaline containing cis-2,6-disubstituents was accomplished by 10 step reactions with a 31% total yield.

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DO - 10.3987/COM-15-13172

M3 - Article

AN - SCOPUS:84935422608

VL - 91

SP - 959

EP - 969

JO - Heterocycles

JF - Heterocycles

SN - 0385-5414

IS - 5

ER -

Divergent synthesis of 2,6-disubstituted piperidine alkaloid, (+)-spectaline by palladium-catalyzed cyclization

Abstract

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