Enantioselective Synthesis of the Key Intermediate of the Acyl-CoA : Cholesterol Acyltransferase (ACAT) Inhibitor (R-106578) Using 2, 2'-Bis(diphenylphosphino)-1, 1'-binaphthyl (BINAP)-Ru(OAc)2 as a Catalyst

Enantioselective Synthesis of the Key Intermediate of the Acyl-CoA : Cholesterol Acyltransferase (ACAT) Inhibitor (R-106578) Using 2, 2'-Bis(diphenylphosphino)-1, 1'-binaphthyl (BINAP)-Ru(OAc)2 as a Catalyst

Acidic segment of an acyl-CoA : cholesterol acyltransferase (ACAT) inhibitor, R-106578 was synthesized by enantioselective hydrogenation of the Z-olefine (9-(Z)) using (R)-2, 2'-bis(diphenylphosphino)-1, 1'-binaphthyl(BINAP)-Ru(OAc)2 as a catalyst in methanol at 100°C, 5kgf/cm2 of H2 press...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 2000/10/01, Vol.48(10), pp.1567-1569
Hauptverfasser: MURAKAMI, Masayuki, KOBAYASHI, Keijiro, HIRAI, Koichi
Format: Artikel
Sprache:eng
Schlagworte:
(R)-BINAP-Ru(OAc)2
ACAT inhibitor
Aliphatic compounds
Catalysis
Chemistry
coumarin derivative
enantioselective hydrogenation
Enzyme Inhibitors - chemical synthesis
Enzyme Inhibitors - chemistry
Exact sciences and technology
Organic chemistry
Organometallic Compounds - chemical synthesis
Organometallic Compounds - chemistry
Preparations and properties
Stereoisomerism
Sterol O-Acyltransferase - antagonists & inhibitors
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Beschreibung
Zusammenfassung:Acidic segment of an acyl-CoA : cholesterol acyltransferase (ACAT) inhibitor, R-106578 was synthesized by enantioselective hydrogenation of the Z-olefine (9-(Z)) using (R)-2, 2'-bis(diphenylphosphino)-1, 1'-binaphthyl(BINAP)-Ru(OAc)2 as a catalyst in methanol at 100°C, 5kgf/cm2 of H2 pressure. The requisite Z-olefine was prepared regioselectively via coumarin derivative (5).
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.48.1567