PMID- 11045470 OWN - NLM STAT- MEDLINE DCOM- 20010208 LR - 20190706 IS - 0009-2363 (Print) IS - 0009-2363 (Linking) VI - 48 IP - 10 DP - 2000 Oct TI - 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. PG - 1567-9 AB - 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 degrees C, 5 kgf/cm2 of H2 pressure. The requisite Z-olefine was prepared regioselectively via coumarin derivative (5). FAU - Murakami, M AU - Murakami M AD - Process Development Laboratories, Sankyo Co., Ltd., Kanagawa, Japan. FAU - Kobayashi, K AU - Kobayashi K FAU - Hirai, K AU - Hirai K LA - eng PT - Journal Article PL - Japan TA - Chem Pharm Bull (Tokyo) JT - Chemical & pharmaceutical bulletin JID - 0377775 RN - 0 (2,2'-bis(diphenylphosphino)-1,1'-binaphthyl-Ru(OAc)2) RN - 0 (Enzyme Inhibitors) RN - 0 (Organometallic Compounds) RN - EC 2.3.1.26 (Sterol O-Acyltransferase) SB - IM MH - Catalysis MH - Enzyme Inhibitors/*chemical synthesis/chemistry MH - Organometallic Compounds/*chemical synthesis/chemistry MH - Stereoisomerism MH - Sterol O-Acyltransferase/*antagonists & inhibitors EDAT- 2000/10/25 11:00 MHDA- 2001/03/03 10:01 CRDT- 2000/10/25 11:00 PHST- 2000/10/25 11:00 [pubmed] PHST- 2001/03/03 10:01 [medline] PHST- 2000/10/25 11:00 [entrez] AID - 10.1248/cpb.48.1567 [doi] PST - ppublish SO - Chem Pharm Bull (Tokyo). 2000 Oct;48(10):1567-9. doi: 10.1248/cpb.48.1567.