First asymmetric total synthesis of (−)-isostemonamine and kinetic analysis of its isomerizations

Takayuki Iwata, Taishi Tomiyama, Satoshi Fujita, Mitsuru Shindo

研究成果: ジャーナルへの寄稿記事

1 引用 (Scopus)

抄録

The first asymmetric total synthesis of (−)-isostemonamine is reported herein. The key reactions include the regioselective oxidation of the diketone, which is reported to be an intermediate in our synthesis of (−)-stemonamine. The chiral high-performance liquid chromatography (HPLC) analysis of the racemization and epimerization of (−)-isostemonamine revealed that isostemonamine isomerizes significantly faster than stemonamine.

元の言語英語
ページ(範囲)712-718
ページ数7
ジャーナルHeterocycles
97
発行部数2
DOI
出版物ステータス出版済み - 1 1 2018

Fingerprint

Isomerization
Kinetics
High performance liquid chromatography
High Pressure Liquid Chromatography
Oxidation
stemonamine

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

これを引用

First asymmetric total synthesis of (−)-isostemonamine and kinetic analysis of its isomerizations. / Iwata, Takayuki; Tomiyama, Taishi; Fujita, Satoshi; Shindo, Mitsuru.

:: Heterocycles, 巻 97, 番号 2, 01.01.2018, p. 712-718.

研究成果: ジャーナルへの寄稿記事

@article{61907ea0229f4c42932d6729c9b63214,
title = "First asymmetric total synthesis of (−)-isostemonamine and kinetic analysis of its isomerizations",
abstract = "The first asymmetric total synthesis of (−)-isostemonamine is reported herein. The key reactions include the regioselective oxidation of the diketone, which is reported to be an intermediate in our synthesis of (−)-stemonamine. The chiral high-performance liquid chromatography (HPLC) analysis of the racemization and epimerization of (−)-isostemonamine revealed that isostemonamine isomerizes significantly faster than stemonamine.",
author = "Takayuki Iwata and Taishi Tomiyama and Satoshi Fujita and Mitsuru Shindo",
year = "2018",
month = "1",
day = "1",
doi = "10.3987/COM-18-S(T)71",
language = "English",
volume = "97",
pages = "712--718",
journal = "Heterocycles",
issn = "0385-5414",
publisher = "Japan Institute of Heterocyclic Chemistry",
number = "2",

}

TY - JOUR

T1 - First asymmetric total synthesis of (−)-isostemonamine and kinetic analysis of its isomerizations

AU - Iwata, Takayuki

AU - Tomiyama, Taishi

AU - Fujita, Satoshi

AU - Shindo, Mitsuru

PY - 2018/1/1

Y1 - 2018/1/1

N2 - The first asymmetric total synthesis of (−)-isostemonamine is reported herein. The key reactions include the regioselective oxidation of the diketone, which is reported to be an intermediate in our synthesis of (−)-stemonamine. The chiral high-performance liquid chromatography (HPLC) analysis of the racemization and epimerization of (−)-isostemonamine revealed that isostemonamine isomerizes significantly faster than stemonamine.

AB - The first asymmetric total synthesis of (−)-isostemonamine is reported herein. The key reactions include the regioselective oxidation of the diketone, which is reported to be an intermediate in our synthesis of (−)-stemonamine. The chiral high-performance liquid chromatography (HPLC) analysis of the racemization and epimerization of (−)-isostemonamine revealed that isostemonamine isomerizes significantly faster than stemonamine.

UR - http://www.scopus.com/inward/record.url?scp=85064527389&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85064527389&partnerID=8YFLogxK

U2 - 10.3987/COM-18-S(T)71

DO - 10.3987/COM-18-S(T)71

M3 - Article

AN - SCOPUS:85064527389

VL - 97

SP - 712

EP - 718

JO - Heterocycles

JF - Heterocycles

SN - 0385-5414

IS - 2

ER -