Synthesis 2015; 47(09): 1238-1244
DOI: 10.1055/s-0034-1380289
psp
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Optically Pure (R)- and (S)-Tetrahydroisoquinoline-1- and -3-Carboxylic Acids

Kaoruko Kurata
a  Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto, 607-8412, Japan   Email: [email protected]
,
Kumiko Inoue
a  Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto, 607-8412, Japan   Email: [email protected]
,
Kazuhiko Nishimura
a  Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto, 607-8412, Japan   Email: [email protected]
,
Naoyuki Hoshiya*
a  Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto, 607-8412, Japan   Email: [email protected]
,
Nobuyuki Kawai*
b  School of Pharmaceutical Sciences, Mukogawa Women’s University, 11-68 Koshien Kyu-bancho, Nishinomiya 663-8179, Japan
,
Junichi Uenishi
a  Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto, 607-8412, Japan   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 20 January 2015

Accepted after revision: 12 February 2015

Publication Date:
12 March 2015 (online)


Abstract

The synthesis of (R)- and (S)-tetrahydroisoquinoline-1-carboxylic acids was achieved from N-Boc-protected (R)- and (S)-1-propenyltetrahydroisoquinoline, respectively, in a three-step sequence of ozonolysis, NaBH4 reduction, oxidation, and deprotection of the N-Boc group. Similarly, (S)-tetrahydroisoquinoline-3-carboxylic acids were obtained from N-Boc-protected (S)-3-(4-phenylbutenyl)tetrahydroisoquinolines. This synthetic route provides tetrahydroisoquinoline ring-based cyclic amino acids in enantiomerically pure form in a practical and efficient manner.

Supporting Information

 
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