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^*

^*Corresponding author for this work

Life Sciences and Bioengineering

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

5 Scopus citations

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.

Original language	English
Pages (from-to)	1939-1945
Number of pages	7
Journal	ChemistrySelect
Volume	6
Issue number	8
DOIs	https://doi.org/10.1002/slct.202004825
State	Published - 2021/02/24

Keywords

Alkaloid
Chiral building block
Divergent synthesis
Heterocycles
Pumiliotoxin

ASJC Scopus subject areas

General Chemistry

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10.1002/slct.202004825

Cite this

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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",

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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

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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

Abstract

Keywords

ASJC Scopus subject areas

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