Divergent Syntheses of Pumiliotoxin-Type Poison-Frog Alkaloids

Takuya Okada; Takanori Ozaki; Taiga Yamamoto; Hirofumi Kasahara; Masashi Kawasaki; Naoki Toyooka

doi:10.1002/slct.202004825

Divergent Syntheses of Pumiliotoxin-Type Poison-Frog Alkaloids

Takuya Okada^*, Takanori Ozaki, Taiga Yamamoto, Hirofumi Kasahara, Masashi Kawasaki, Naoki Toyooka^*

^*この論文の責任著者

工学科　生命工学コース

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

5 被引用数 (Scopus)

抄録

Over 800 lipophilic alkaloids have been detected from the skin extracts of poison frogs. Pumiliotoxins (PTXs) are a large class of poison-frog alkaloids, and various congeners of PTXs have been detected to date. However, no exhaustive and effective syntheses of PTXs and their congeners have been reported. Herein, we describe the divergent syntheses of PTX 209F, hPTX 223G, 8-deoxy-PTX 193H, 9-deoxy-hPTX 207O, 8-desmethyl-PTX 195, and 9-desmethyl-hPTX 209H from the common chiral building block (2R,3S)-ethyl 1-allyl-3-hydroxy-6-oxopiperidine-2-carboxylate (−)-1.

本文言語	英語
ページ（範囲）	1939-1945
ページ数	7
ジャーナル	ChemistrySelect
巻	6
号	8
DOI	https://doi.org/10.1002/slct.202004825
出版ステータス	出版済み - 2021/02/24

ASJC Scopus 主題領域

化学一般

文献へのアクセス

10.1002/slct.202004825

引用スタイル

@article{800ef387f0b7466d9765a0778ea34ff1,

title = "Divergent Syntheses of Pumiliotoxin-Type Poison-Frog Alkaloids",

abstract = "Over 800 lipophilic alkaloids have been detected from the skin extracts of poison frogs. Pumiliotoxins (PTXs) are a large class of poison-frog alkaloids, and various congeners of PTXs have been detected to date. However, no exhaustive and effective syntheses of PTXs and their congeners have been reported. Herein, we describe the divergent syntheses of PTX 209F, hPTX 223G, 8-deoxy-PTX 193H, 9-deoxy-hPTX 207O, 8-desmethyl-PTX 195, and 9-desmethyl-hPTX 209H from the common chiral building block (2R,3S)-ethyl 1-allyl-3-hydroxy-6-oxopiperidine-2-carboxylate (−)-1.",

keywords = "Alkaloid, Chiral building block, Divergent synthesis, Heterocycles, Pumiliotoxin",

author = "Takuya Okada and Takanori Ozaki and Taiga Yamamoto and Hirofumi Kasahara and Masashi Kawasaki and Naoki Toyooka",

note = "Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH",

year = "2021",

month = feb,

day = "24",

doi = "10.1002/slct.202004825",

language = "英語",

volume = "6",

pages = "1939--1945",

journal = "ChemistrySelect",

issn = "2365-6549",

publisher = "Wiley-Blackwell Publishing Ltd",

number = "8",

}

TY - JOUR

T1 - Divergent Syntheses of Pumiliotoxin-Type Poison-Frog Alkaloids

AU - Okada, Takuya

AU - Ozaki, Takanori

AU - Yamamoto, Taiga

AU - Kasahara, Hirofumi

AU - Kawasaki, Masashi

AU - Toyooka, Naoki

PY - 2021/2/24

Y1 - 2021/2/24

N2 - Over 800 lipophilic alkaloids have been detected from the skin extracts of poison frogs. Pumiliotoxins (PTXs) are a large class of poison-frog alkaloids, and various congeners of PTXs have been detected to date. However, no exhaustive and effective syntheses of PTXs and their congeners have been reported. Herein, we describe the divergent syntheses of PTX 209F, hPTX 223G, 8-deoxy-PTX 193H, 9-deoxy-hPTX 207O, 8-desmethyl-PTX 195, and 9-desmethyl-hPTX 209H from the common chiral building block (2R,3S)-ethyl 1-allyl-3-hydroxy-6-oxopiperidine-2-carboxylate (−)-1.

AB - Over 800 lipophilic alkaloids have been detected from the skin extracts of poison frogs. Pumiliotoxins (PTXs) are a large class of poison-frog alkaloids, and various congeners of PTXs have been detected to date. However, no exhaustive and effective syntheses of PTXs and their congeners have been reported. Herein, we describe the divergent syntheses of PTX 209F, hPTX 223G, 8-deoxy-PTX 193H, 9-deoxy-hPTX 207O, 8-desmethyl-PTX 195, and 9-desmethyl-hPTX 209H from the common chiral building block (2R,3S)-ethyl 1-allyl-3-hydroxy-6-oxopiperidine-2-carboxylate (−)-1.

KW - Alkaloid

KW - Chiral building block

KW - Divergent synthesis

KW - Heterocycles

KW - Pumiliotoxin

UR - http://www.scopus.com/inward/record.url?scp=85101516555&partnerID=8YFLogxK

U2 - 10.1002/slct.202004825

DO - 10.1002/slct.202004825

M3 - 学術論文

AN - SCOPUS:85101516555

SN - 2365-6549

VL - 6

SP - 1939

EP - 1945

JO - ChemistrySelect

JF - ChemistrySelect

IS - 8

ER -

Divergent Syntheses of Pumiliotoxin-Type Poison-Frog Alkaloids

抄録

ASJC Scopus 主題領域

文献へのアクセス

フィンガープリント

引用スタイル