新产品编号:1894163

Chemical Name: 4,8,8-Trimethyl-9(R),10(R)-bis[4(R),7,7-trimethyl-2-oxabicyclo[2.2.1]hept-1-ylcarbonyloxy]-1,8,9,10-tetrahydro-2H-pyrano[2,3-h]quinolin-2-one
项目整合开发状态: Biological Testing
项目研究机构: Biotech Research Laboratories (Originator), University of North Carolina (Originator)
合成路线:7-Aminoquinolin-2-one (III) was prepared by Knorr cyclization of m-phenylenediamine (I) with ethyl acetoacetate (II).Subsequent diazotization of (II),followed by acid hydrolysis gave rise to the 7-hydroxyquinolinone (IV).Alkylation of (IV) with 3-chloro-3-methylbut-1-yne (V),followed by Claisen rearrangement of the resulting propargyl ether (V) afforded the pyranoquinolinone (VII).This was protected as the N-Boc derivative (VIII) by treatment with Boc2O and Et3N.Sharpless asymmetric dihydroxylation of (VIII) using dihydroquinine 2,5-diphenyl-4,6-pyrimidinediyl diether ((DHQ)2-PYR) as the chiral catalyst furnished the (R,R)-diol (IX),which was esterified with (-)-(S)-camphanoyl chloride (X) to produce diester (XI).The Boc protecting group of (XI) was finally removed by treatment with trifluoroacetic acid.