Abstract
Preparation of both enantiomeric methyl jasmonates 1 was achieved via lipase-catalyzed resolution of (±)-methyl 7-epicucurbate 3. Lipase P (Amano) provided good selectivity both for acylation of (±)-3 (E = 370) and hydrolysis of the corresponding acetate (E = 41). Resolution of (±)-methyl 6,7-diepicucurbate 2 gave poor results. It was found that the (6R,7S)-configuration was suitable for the selective enzymatic reaction and the C-(3) stereochemistry of the substrate did not influence the enzymatic reaction.
| Original language | English |
|---|---|
| Pages (from-to) | 1035-1038 |
| Number of pages | 4 |
| Journal | Tetrahedron Asymmetry |
| Volume | 12 |
| Issue number | 7 |
| DOIs | |
| Publication status | Published - May 8 2001 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Inorganic Chemistry
- Organic Chemistry
- Materials Chemistry
- Drug Discovery
Cite this
Lipase-catalyzed preparation of both enantiomers of methyl jasmonate. / Kiyota, Hiromasa; Higashi, Emi; Koike, Takanori; Oritani, Takayuki.
In: Tetrahedron Asymmetry, Vol. 12, No. 7, 08.05.2001, p. 1035-1038.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Lipase-catalyzed preparation of both enantiomers of methyl jasmonate
AU - Kiyota, Hiromasa
AU - Higashi, Emi
AU - Koike, Takanori
AU - Oritani, Takayuki
PY - 2001/5/8
Y1 - 2001/5/8
N2 - Preparation of both enantiomeric methyl jasmonates 1 was achieved via lipase-catalyzed resolution of (±)-methyl 7-epicucurbate 3. Lipase P (Amano) provided good selectivity both for acylation of (±)-3 (E = 370) and hydrolysis of the corresponding acetate (E = 41). Resolution of (±)-methyl 6,7-diepicucurbate 2 gave poor results. It was found that the (6R,7S)-configuration was suitable for the selective enzymatic reaction and the C-(3) stereochemistry of the substrate did not influence the enzymatic reaction.
AB - Preparation of both enantiomeric methyl jasmonates 1 was achieved via lipase-catalyzed resolution of (±)-methyl 7-epicucurbate 3. Lipase P (Amano) provided good selectivity both for acylation of (±)-3 (E = 370) and hydrolysis of the corresponding acetate (E = 41). Resolution of (±)-methyl 6,7-diepicucurbate 2 gave poor results. It was found that the (6R,7S)-configuration was suitable for the selective enzymatic reaction and the C-(3) stereochemistry of the substrate did not influence the enzymatic reaction.
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UR - http://www.scopus.com/inward/citedby.url?scp=0035826556&partnerID=8YFLogxK
U2 - 10.1016/S0957-4166(01)00169-0
DO - 10.1016/S0957-4166(01)00169-0
M3 - Article
VL - 12
SP - 1035
EP - 1038
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
SN - 0957-4166
IS - 7
ER -