Development of an asymmetric formal synthesis of (−)-quinagolide enzymatic resolution and stereoselective iminium ion reduction
The stereoselective reduction of a diastereoisomeric mixture of benzo[ g ]octahydroquinolinium ion was examined in detail. A diastereoselective borohydride reduction in combination with an efficient deacylative enzymatic resolution of its β-aminoester precursor are the key steps for a stereoselectiv...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2023-08, Vol.21 (31), p.6389-6396 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Comparini, Lucrezia Margherita Menichetti, Andrea Favero, Lucilla Di Pietro, Sebastiano Badalassi, Fabrizio Ryberg, Per Pineschi, Mauro |
| description | The stereoselective reduction of a diastereoisomeric mixture of benzo[
g
]octahydroquinolinium ion was examined in detail. A diastereoselective borohydride reduction in combination with an efficient deacylative enzymatic resolution of its β-aminoester precursor are the key steps for a stereoselective installation of the three chiral centres present in the (3
S
,4a
S
,10a
R
)-eutomer of the medicinal drug quinagolide. The obtained data paves the way for an easy and practical attainment of chiral 3-substituted octahydrobenzo[
g
]quinolines that are privileged structures in medicinal chemistry.
The study of the reduction of a benzo[
g
]octahydroquinolinium ion was examined in detail under different perspectives until we found a viable solution to get an advanced chiral intermediate of (3
S
,4a
S
,10a
R
)-(−)-quinagolide as a single stereoisomer. |
| doi_str_mv | 10.1039/d3ob00946g |
| format | Article |
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g
]octahydroquinolinium ion was examined in detail. A diastereoselective borohydride reduction in combination with an efficient deacylative enzymatic resolution of its β-aminoester precursor are the key steps for a stereoselective installation of the three chiral centres present in the (3
S
,4a
S
,10a
R
)-eutomer of the medicinal drug quinagolide. The obtained data paves the way for an easy and practical attainment of chiral 3-substituted octahydrobenzo[
g
]quinolines that are privileged structures in medicinal chemistry.
The study of the reduction of a benzo[
g
]octahydroquinolinium ion was examined in detail under different perspectives until we found a viable solution to get an advanced chiral intermediate of (3
S
,4a
S
,10a
R
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g
]octahydroquinolinium ion was examined in detail. A diastereoselective borohydride reduction in combination with an efficient deacylative enzymatic resolution of its β-aminoester precursor are the key steps for a stereoselective installation of the three chiral centres present in the (3
S
,4a
S
,10a
R
)-eutomer of the medicinal drug quinagolide. The obtained data paves the way for an easy and practical attainment of chiral 3-substituted octahydrobenzo[
g
]quinolines that are privileged structures in medicinal chemistry.
The study of the reduction of a benzo[
g
]octahydroquinolinium ion was examined in detail under different perspectives until we found a viable solution to get an advanced chiral intermediate of (3
S
,4a
S
,10a
R
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g
]octahydroquinolinium ion was examined in detail. A diastereoselective borohydride reduction in combination with an efficient deacylative enzymatic resolution of its β-aminoester precursor are the key steps for a stereoselective installation of the three chiral centres present in the (3
S
,4a
S
,10a
R
)-eutomer of the medicinal drug quinagolide. The obtained data paves the way for an easy and practical attainment of chiral 3-substituted octahydrobenzo[
g
]quinolines that are privileged structures in medicinal chemistry.
The study of the reduction of a benzo[
g
]octahydroquinolinium ion was examined in detail under different perspectives until we found a viable solution to get an advanced chiral intermediate of (3
S
,4a
S
,10a
R
)-(−)-quinagolide as a single stereoisomer.</abstract><doi>10.1039/d3ob00946g</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2023-08, Vol.21 (31), p.6389-6396 |
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| language | |
| recordid | cdi_rsc_primary_d3ob00946g |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| title | Development of an asymmetric formal synthesis of (−)-quinagolide enzymatic resolution and stereoselective iminium ion reduction |
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