A new and efficient chemoenzymatic route to both enantiomers of α ′-acetoxy-α-methyl and γ-hydroxy-α-methyl cyclic enones
Graphic A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting α ′-acetoxy-α-methyl and γ-hydroxy-α-methyl cyclic enones starting from α-methyl-β-methoxy cyclic enones is reported. Manganese(III) acetate-mediated acetoxylation followed by the enzyme-mediated hydrolysis o...
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| Published in | Tetrahedron: asymmetry Vol. 15; no. 5; pp. 777 - 781 |
|---|---|
| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
OXFORD
Elsevier Ltd
08.03.2004
Elsevier |
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| Abstract | Graphic
A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting α
′-acetoxy-α-methyl and γ-hydroxy-α-methyl cyclic enones starting from α-methyl-β-methoxy cyclic enones is reported. Manganese(III) acetate-mediated acetoxylation followed by the enzyme-mediated hydrolysis of α
′-acetoxy enone provides acetoxy enones
1a
and
2a
and hydroxy enones
1b
and
2b
with high enantiomeric excesses in good yields. The reduction of the acetoxy and hydroxy enones furnished both enantiomers of γ-hydroxy-α-methyl cyclic enones
3
and
4
in a high enantiomeric excess. |
|---|---|
| AbstractList | A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting alpha'-acetoxy-alpha-methyl and gamma-hydroxy-alpha-methyl cyclic enones starting from alpha-methyl-beta-methoxy cyclic enones is reported. Manganese(Ill) acetate-mediated acetoxylation followed by the enzyme-mediated hydrolysis of alpha'-acetoxy enone provides acetoxy enones 1a and 2a and hydroxy enones 1b and 2b with high enantiomeric excesses in good yields. The reduction of the acetoxy and hydroxy enones furnished both enantiomers of gamma-hydroxy-alpha-methyl cyclic enones 3 and 4 in a high enantiomeric excess. (C) 2003 Elsevier Ltd. All rights reserved. Graphic A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting α ′-acetoxy-α-methyl and γ-hydroxy-α-methyl cyclic enones starting from α-methyl-β-methoxy cyclic enones is reported. Manganese(III) acetate-mediated acetoxylation followed by the enzyme-mediated hydrolysis of α ′-acetoxy enone provides acetoxy enones 1a and 2a and hydroxy enones 1b and 2b with high enantiomeric excesses in good yields. The reduction of the acetoxy and hydroxy enones furnished both enantiomers of γ-hydroxy-α-methyl cyclic enones 3 and 4 in a high enantiomeric excess. |
| Author | Köse, Elif Fındık, Hamide Demir, Ayhan S. |
| Author_xml | – sequence: 1 givenname: Ayhan S. surname: Demir fullname: Demir, Ayhan S. email: asdemir@metu.edu.tr – sequence: 2 givenname: Hamide surname: Fındık fullname: Fındık, Hamide – sequence: 3 givenname: Elif surname: Köse fullname: Köse, Elif |
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| CitedBy_id | crossref_primary_10_1016_j_tetlet_2009_02_016 crossref_primary_10_1016_j_tet_2008_05_004 crossref_primary_10_1016_j_tet_2016_03_095 crossref_primary_10_1007_s11030_009_9144_x crossref_primary_10_1021_ar900196n crossref_primary_10_31015_jaefs_2023_2_4 crossref_primary_10_1039_c1gc15160f crossref_primary_10_1002_adsc_201700711 crossref_primary_10_1016_j_molcatb_2014_10_015 crossref_primary_10_1016_j_tetasy_2006_01_025 crossref_primary_10_1016_j_tetasy_2004_07_028 |
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| Keywords | OXIDATION MANGANESE(III) ACETATE ACYLOXY 4-SUBSTITUTED 5-HYDROXY-3-OXOCYCLOPENTENES PROSTAGLANDIN COMBINATION INHIBITOR FACILE DERIVATIVES GRIGNARD |
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A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting α
′-acetoxy-α-methyl and γ-hydroxy-α-methyl cyclic enones starting... A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting alpha'-acetoxy-alpha-methyl and gamma-hydroxy-alpha-methyl cyclic enones... |
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| SubjectTerms | Chemistry Chemistry, Inorganic & Nuclear Chemistry, Organic Chemistry, Physical Physical Sciences Science & Technology |
| Title | A new and efficient chemoenzymatic route to both enantiomers of α ′-acetoxy-α-methyl and γ-hydroxy-α-methyl cyclic enones |
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