Synthesis of 8-deoxypumiliotoxin 193H and 9-deoxyhomopumiliotoxin 207O

Takuya Okada; Taiga Yamamoto; Daiki Kato; Masashi Kawasaki; Ralph A. Saporito; Naoki Toyooka

doi:10.1016/j.tetlet.2018.09.015

Synthesis of 8-deoxypumiliotoxin 193H and 9-deoxyhomopumiliotoxin 207O

Takuya Okada^*, Taiga Yamamoto, Daiki Kato, Masashi Kawasaki, Ralph A. Saporito, Naoki Toyooka

^*Corresponding author for this work

Life Sciences and Bioengineering

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

11 Scopus citations

Abstract

The asymmetric synthesis of 8-deoxypumiliotoxin 193H and 9-deoxyhomopumiliotoxin 207O has been achieved, starting from both enantiomers of (+)- and (−)-10. Enantiomerically pure alcohols (+)- and (−)-10 were obtained by lipase-mediated kinetic resolution of racemic 10, which was prepared in 3 steps from new lactam-type building block (−)-8 in a highly stereoselective manner.

Original language	English
Pages (from-to)	3797-3800
Number of pages	4
Journal	Tetrahedron Letters
Volume	59
Issue number	42
DOIs	https://doi.org/10.1016/j.tetlet.2018.09.015
State	Published - 2018/10/17

Keywords

8-Deoxypumiliotoxin 193H
9-Deoxyhomopumiliotoxin 207O
Asymmetric synthesis
Neotropical poison frog
Pumiliotoxin

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2018.09.015

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@article{506db34465a74232accee74485b61076,

title = "Synthesis of 8-deoxypumiliotoxin 193H and 9-deoxyhomopumiliotoxin 207O",

abstract = "The asymmetric synthesis of 8-deoxypumiliotoxin 193H and 9-deoxyhomopumiliotoxin 207O has been achieved, starting from both enantiomers of (+)- and (−)-10. Enantiomerically pure alcohols (+)- and (−)-10 were obtained by lipase-mediated kinetic resolution of racemic 10, which was prepared in 3 steps from new lactam-type building block (−)-8 in a highly stereoselective manner.",

keywords = "8-Deoxypumiliotoxin 193H, 9-Deoxyhomopumiliotoxin 207O, Asymmetric synthesis, Neotropical poison frog, Pumiliotoxin",

author = "Takuya Okada and Taiga Yamamoto and Daiki Kato and Masashi Kawasaki and Saporito, {Ralph A.} and Naoki Toyooka",

note = "Publisher Copyright: {\textcopyright} 2018",

year = "2018",

month = oct,

day = "17",

doi = "10.1016/j.tetlet.2018.09.015",

language = "英語",

volume = "59",

pages = "3797--3800",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Synthesis of 8-deoxypumiliotoxin 193H and 9-deoxyhomopumiliotoxin 207O

AU - Okada, Takuya

AU - Yamamoto, Taiga

AU - Kato, Daiki

AU - Kawasaki, Masashi

AU - Saporito, Ralph A.

AU - Toyooka, Naoki

PY - 2018/10/17

Y1 - 2018/10/17

N2 - The asymmetric synthesis of 8-deoxypumiliotoxin 193H and 9-deoxyhomopumiliotoxin 207O has been achieved, starting from both enantiomers of (+)- and (−)-10. Enantiomerically pure alcohols (+)- and (−)-10 were obtained by lipase-mediated kinetic resolution of racemic 10, which was prepared in 3 steps from new lactam-type building block (−)-8 in a highly stereoselective manner.

AB - The asymmetric synthesis of 8-deoxypumiliotoxin 193H and 9-deoxyhomopumiliotoxin 207O has been achieved, starting from both enantiomers of (+)- and (−)-10. Enantiomerically pure alcohols (+)- and (−)-10 were obtained by lipase-mediated kinetic resolution of racemic 10, which was prepared in 3 steps from new lactam-type building block (−)-8 in a highly stereoselective manner.

KW - 8-Deoxypumiliotoxin 193H

KW - 9-Deoxyhomopumiliotoxin 207O

KW - Asymmetric synthesis

KW - Neotropical poison frog

KW - Pumiliotoxin

UR - http://www.scopus.com/inward/record.url?scp=85053108481&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2018.09.015

DO - 10.1016/j.tetlet.2018.09.015

M3 - 学術論文

AN - SCOPUS:85053108481

SN - 0040-4039

VL - 59

SP - 3797

EP - 3800

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 42

ER -

Synthesis of 8-deoxypumiliotoxin 193H and 9-deoxyhomopumiliotoxin 207O

Abstract

Keywords

ASJC Scopus subject areas

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