Multiple production of α,α-disubstituted amino acid derivatives through direct chemical derivatization of natural plant extracts

An apparently difficult but successful route

Keisuke Tomohara, Tomohiro Ito, Kota Furusawa, Naoto Hasegawa, Kiyoshi Tsuge, Atsushi Kato, Isao Adachi

研究成果: ジャーナルへの寄稿記事

4 引用 (Scopus)

抄録

Natural plant extracts are rich in chemical entities with structural, stereochemical, and functional group diversity and complexity. Here, such privileged extracts were effectively harnessed as synthetic platforms for multiple production of α,α-disubstituted amino acid derivatives through the direct chemical derivatization under the Bucherer–Bergs reaction conditions. The derivatization proceeded with chemoselectivity, enough to identify a series of novel hydantoins 5 and 10–13 and cyclic carbamates 6 and 14–16, starting with the ethyl acetate extracts of Paeonia suffruticosa and Zingiber officinale, respectively. The substrate extracts were definitely selected through the quantitative and qualitative analyses of 68 natural plant candidates.

元の言語英語
ページ(範囲)3143-3147
ページ数5
ジャーナルTetrahedron Letters
58
発行部数32
DOI
出版物ステータス出版済み - 1 1 2017
外部発表Yes

Fingerprint

Paeonia
Hydantoins
Ginger
Carbamates
Plant Extracts
Functional groups
Derivatives
Amino Acids
Substrates
ethyl acetate

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

これを引用

Multiple production of α,α-disubstituted amino acid derivatives through direct chemical derivatization of natural plant extracts : An apparently difficult but successful route. / Tomohara, Keisuke; Ito, Tomohiro; Furusawa, Kota; Hasegawa, Naoto; Tsuge, Kiyoshi; Kato, Atsushi; Adachi, Isao.

:: Tetrahedron Letters, 巻 58, 番号 32, 01.01.2017, p. 3143-3147.

研究成果: ジャーナルへの寄稿記事

Tomohara, Keisuke ; Ito, Tomohiro ; Furusawa, Kota ; Hasegawa, Naoto ; Tsuge, Kiyoshi ; Kato, Atsushi ; Adachi, Isao. / Multiple production of α,α-disubstituted amino acid derivatives through direct chemical derivatization of natural plant extracts : An apparently difficult but successful route. :: Tetrahedron Letters. 2017 ; 巻 58, 番号 32. pp. 3143-3147.
@article{d6585192b90f4c338d87a133a25dc9e9,
title = "Multiple production of α,α-disubstituted amino acid derivatives through direct chemical derivatization of natural plant extracts: An apparently difficult but successful route",
abstract = "Natural plant extracts are rich in chemical entities with structural, stereochemical, and functional group diversity and complexity. Here, such privileged extracts were effectively harnessed as synthetic platforms for multiple production of α,α-disubstituted amino acid derivatives through the direct chemical derivatization under the Bucherer–Bergs reaction conditions. The derivatization proceeded with chemoselectivity, enough to identify a series of novel hydantoins 5 and 10–13 and cyclic carbamates 6 and 14–16, starting with the ethyl acetate extracts of Paeonia suffruticosa and Zingiber officinale, respectively. The substrate extracts were definitely selected through the quantitative and qualitative analyses of 68 natural plant candidates.",
author = "Keisuke Tomohara and Tomohiro Ito and Kota Furusawa and Naoto Hasegawa and Kiyoshi Tsuge and Atsushi Kato and Isao Adachi",
year = "2017",
month = "1",
day = "1",
doi = "10.1016/j.tetlet.2017.06.087",
language = "English",
volume = "58",
pages = "3143--3147",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "32",

}

TY - JOUR

T1 - Multiple production of α,α-disubstituted amino acid derivatives through direct chemical derivatization of natural plant extracts

T2 - An apparently difficult but successful route

AU - Tomohara, Keisuke

AU - Ito, Tomohiro

AU - Furusawa, Kota

AU - Hasegawa, Naoto

AU - Tsuge, Kiyoshi

AU - Kato, Atsushi

AU - Adachi, Isao

PY - 2017/1/1

Y1 - 2017/1/1

N2 - Natural plant extracts are rich in chemical entities with structural, stereochemical, and functional group diversity and complexity. Here, such privileged extracts were effectively harnessed as synthetic platforms for multiple production of α,α-disubstituted amino acid derivatives through the direct chemical derivatization under the Bucherer–Bergs reaction conditions. The derivatization proceeded with chemoselectivity, enough to identify a series of novel hydantoins 5 and 10–13 and cyclic carbamates 6 and 14–16, starting with the ethyl acetate extracts of Paeonia suffruticosa and Zingiber officinale, respectively. The substrate extracts were definitely selected through the quantitative and qualitative analyses of 68 natural plant candidates.

AB - Natural plant extracts are rich in chemical entities with structural, stereochemical, and functional group diversity and complexity. Here, such privileged extracts were effectively harnessed as synthetic platforms for multiple production of α,α-disubstituted amino acid derivatives through the direct chemical derivatization under the Bucherer–Bergs reaction conditions. The derivatization proceeded with chemoselectivity, enough to identify a series of novel hydantoins 5 and 10–13 and cyclic carbamates 6 and 14–16, starting with the ethyl acetate extracts of Paeonia suffruticosa and Zingiber officinale, respectively. The substrate extracts were definitely selected through the quantitative and qualitative analyses of 68 natural plant candidates.

UR - http://www.scopus.com/inward/record.url?scp=85022046026&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85022046026&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2017.06.087

DO - 10.1016/j.tetlet.2017.06.087

M3 - Article

VL - 58

SP - 3143

EP - 3147

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 32

ER -