Asymmetric synthesis of (-)- and (+)-kainic acid using a planar chiral amide as a chiral building block

Katsuhiko Tomooka; Toshiyuki Akiyama; Phewluangdee Man; Masaki Suzuki

doi:10.1016/j.tetlet.2008.08.058

Asymmetric synthesis of (-)- and (+)-kainic acid using a planar chiral amide as a chiral building block

Katsuhiko Tomooka, Toshiyuki Akiyama, Phewluangdee Man, Masaki Suzuki

Department of Applied Molecular Chemistry

Research output: Contribution to journal › Article › peer-review

40 Citations (Scopus)

Abstract

Both enantiomers of kainic acid have been synthesized from enantioenriched planar chiral cyclic amide 2a. The C3 and C4 stereocenters in the pyrrolidine ring were constructed by transannular Cope rearrangement of 2a, and the carboxyl group at the C2 position was introduced through lithiation followed by a carboxylation in the presence of an external chiral ligand.

Original language	English
Pages (from-to)	6327-6329
Number of pages	3
Journal	Tetrahedron Letters
Volume	49
Issue number	44
DOIs	https://doi.org/10.1016/j.tetlet.2008.08.058
Publication status	Published - Oct 27 2008

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2008.08.058

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title = "Asymmetric synthesis of (-)- and (+)-kainic acid using a planar chiral amide as a chiral building block",

abstract = "Both enantiomers of kainic acid have been synthesized from enantioenriched planar chiral cyclic amide 2a. The C3 and C4 stereocenters in the pyrrolidine ring were constructed by transannular Cope rearrangement of 2a, and the carboxyl group at the C2 position was introduced through lithiation followed by a carboxylation in the presence of an external chiral ligand.",

author = "Katsuhiko Tomooka and Toshiyuki Akiyama and Phewluangdee Man and Masaki Suzuki",

note = "Funding Information: This research was supported in part by a Grant-in-Aid for Scientific Research in Priority Areas (A) {\textquoteleft}Creation of Biologically Functional Molecules{\textquoteright} from the Ministry of Education, Culture, Sports, Science and Technology, Japan, and The Naito Foundation. ",

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journal = "Tetrahedron Letters",

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T1 - Asymmetric synthesis of (-)- and (+)-kainic acid using a planar chiral amide as a chiral building block

AU - Tomooka, Katsuhiko

AU - Akiyama, Toshiyuki

AU - Man, Phewluangdee

AU - Suzuki, Masaki

N1 - Funding Information: This research was supported in part by a Grant-in-Aid for Scientific Research in Priority Areas (A) ‘Creation of Biologically Functional Molecules’ from the Ministry of Education, Culture, Sports, Science and Technology, Japan, and The Naito Foundation.

PY - 2008/10/27

Y1 - 2008/10/27

N2 - Both enantiomers of kainic acid have been synthesized from enantioenriched planar chiral cyclic amide 2a. The C3 and C4 stereocenters in the pyrrolidine ring were constructed by transannular Cope rearrangement of 2a, and the carboxyl group at the C2 position was introduced through lithiation followed by a carboxylation in the presence of an external chiral ligand.

AB - Both enantiomers of kainic acid have been synthesized from enantioenriched planar chiral cyclic amide 2a. The C3 and C4 stereocenters in the pyrrolidine ring were constructed by transannular Cope rearrangement of 2a, and the carboxyl group at the C2 position was introduced through lithiation followed by a carboxylation in the presence of an external chiral ligand.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

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ER -

Asymmetric synthesis of (-)- and (+)-kainic acid using a planar chiral amide as a chiral building block

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