Synthesis of (-)-Methyl Shikimate via Enzymatic Resolution of (1S*, 4R*, 5R*)-4-Hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one

Takayuki Oritani; Rumi Ueda; Hiromasa Kiyota

doi:10.1271/bbb.65.2106

Synthesis of (-)-Methyl Shikimate via Enzymatic Resolution of (1S, 4R, 5R*)-4-Hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one

Takayuki Oritani, Rumi Ueda, Hiromasa Kiyota

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

3 Citations (Scopus)

Abstract

The synthesis of methyl (-)-shikimate [(-)-2] was achieved via lipase-catalyzed optical resolution of (1S*, 4R*, 5R*)-4-hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one (3). Transesterification of (±)-3 and vinyl acetate with lipase MY and subsequent hydrolysis gave optically pure (-)-3. This compound was converted to (-)-2 in two steps.

Original language	English
Pages (from-to)	2106-2109
Number of pages	4
Journal	Bioscience, Biotechnology and Biochemistry
Volume	65
Issue number	9
DOIs	https://doi.org/10.1271/bbb.65.2106
Publication status	Published - Sept 2001
Externally published	Yes

Keywords

(1S*, 4R*, 5R*)-4-hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one
Hydrolysis
Lipase
Shikimic acid
Transesterification

ASJC Scopus subject areas

Biotechnology
Analytical Chemistry
Biochemistry
Applied Microbiology and Biotechnology
Molecular Biology
Organic Chemistry

Access to Document

10.1271/bbb.65.2106

Cite this

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title = "Synthesis of (-)-Methyl Shikimate via Enzymatic Resolution of (1S*, 4R*, 5R*)-4-Hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one",

abstract = "The synthesis of methyl (-)-shikimate [(-)-2] was achieved via lipase-catalyzed optical resolution of (1S*, 4R*, 5R*)-4-hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one (3). Transesterification of (±)-3 and vinyl acetate with lipase MY and subsequent hydrolysis gave optically pure (-)-3. This compound was converted to (-)-2 in two steps.",

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author = "Takayuki Oritani and Rumi Ueda and Hiromasa Kiyota",

year = "2001",

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AU - Oritani, Takayuki

AU - Ueda, Rumi

AU - Kiyota, Hiromasa

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N2 - The synthesis of methyl (-)-shikimate [(-)-2] was achieved via lipase-catalyzed optical resolution of (1S*, 4R*, 5R*)-4-hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one (3). Transesterification of (±)-3 and vinyl acetate with lipase MY and subsequent hydrolysis gave optically pure (-)-3. This compound was converted to (-)-2 in two steps.

AB - The synthesis of methyl (-)-shikimate [(-)-2] was achieved via lipase-catalyzed optical resolution of (1S*, 4R*, 5R*)-4-hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one (3). Transesterification of (±)-3 and vinyl acetate with lipase MY and subsequent hydrolysis gave optically pure (-)-3. This compound was converted to (-)-2 in two steps.

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KW - Hydrolysis

KW - Lipase

KW - Shikimic acid

KW - Transesterification

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