title: Optically pure γ-butyrolactones and epoxy esters via two stereocentered HKR of 3-substituted epoxy esters: a formal synthesis of (-)-paroxetine, Ro 67-8867 and (+)-eldanolide.
abstract: The HKR of racemic anti- or syn-3-substituted epoxy esters catalyzed by a Co(III)salen complex provides ready access to the corresponding enantioenriched 3,4-disubstituted γ-butyrolactones and 3-substituted epoxy esters. This strategy has been successfully employed in the formal synthesis of biologically active 3,4-disubstituted piperidine derivatives, (-)-paroxetine and Ro 67-8867 and a natural product, (+)-eldanolide.
authors: Chemical Engineering and Process Development Division, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India.
authors: Dattatray A
authors: DA
authors: Devalankar
authors: Pratibha U
authors: PU
authors: Karabal
authors: Arumugam
authors: A
authors: Sudalai
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000737:chemistry*; D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D006868:Hydrolysis; D007700:Kinetics; D015394:Molecular Structure; D055620:Optical Phenomena; D009942:Organometallic Compounds / Q000737:chemistry; D017374:Paroxetine / Q000138:chemical synthesis* / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C431790:6-methyl-4,4,5-trifluorohept-1,5-dien-3-ol; D000466:Alkadienes; D004852:Epoxy Compounds; D004952:Esters; D009942:Organometallic Compounds; D010880:Piperidines; C584172:Ro 67-8867; D017374:Paroxetine; D015107:4-Butyrolactone