Stereoselective synthesis of a new muscarinic M3 receptor antagonist, J-104129.
A diastereoselective synthesis of J-104129 (1) was developed. A key step of this synthesis was Michael addition of enolate generated from cis-chiral dioxolane 2 to cyclopentenone, followed by hydrogenolysis of the resultant enol triflate 4. A mixture of cyclopentyldioxolane (5, 6) was hydrolyzed with sodium hydroxide to yield carboxylic acid 7 in 86% ee.
Mitsuya
M
M
Banyu Tsukuba Research Institute in collaboration with Merck Research Laboratories, Ibaraki, Japan.
Kawakami
K
K
Ogino
Y
Y
Miura
K
K
Mase
T
T
D000475:Alkenes / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D015394:Molecular Structure; D018727:Muscarinic Antagonists / Q000138:chemical synthesis* / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis*; D043587:Receptor, Muscarinic M3; D011976:Receptors, Muscarinic
D000475:Alkenes; C121300:J 104129; D018727:Muscarinic Antagonists; D010880:Piperidines; D043587:Receptor, Muscarinic M3; D011976:Receptors, Muscarinic