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
N1 - Publisher Copyright:
© 2017 Elsevier Ltd
PY - 2017
Y1 - 2017
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
AN - SCOPUS:85022046026
SN - 0040-4039
VL - 58
SP - 3143
EP - 3147
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 32
ER -