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

Research output: Contribution to journalArticle

4 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)3143-3147
Number of pages5
JournalTetrahedron Letters
Volume58
Issue number32
DOIs
Publication statusPublished - Jan 1 2017
Externally publishedYes

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

Cite this

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.

In: Tetrahedron Letters, Vol. 58, No. 32, 01.01.2017, p. 3143-3147.

Research output: Contribution to journalArticle

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. In: Tetrahedron Letters. 2017 ; Vol. 58, No. 32. pp. 3143-3147.
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