Vicinal dianion of triethyl ethanetricarboxylate: Syntheses of (±)-lichesterinic acid, (±)-phaseolinic acid, (±)-nephromopsinic acid, (±)-rocellaric acid, and (±)-dihydroprotolichesterinic acid

Manat PohmakotrWacharee HarnyingPatoomratana TuchindaVichai ReutrakulMahidol University2018-07-242018-07-242002-01-01Helvetica Chimica Acta. Vol.85, No.11 (2002), 3792-38130018019X2-s2.0-0036943889https://repository.li.mahidol.ac.th/handle/20.500.14594/20097The vicinal dianion 2 derived from triethyl ethanetricarboxylate reacted regioselectively with aldehydes and ketones at C(β) to provide paraconic acid derivatives 5a-f in moderate to high yields as mixtures of diastereoisomers. The paraconic acid derivatives 5e and 5f were utilized as the starting materials for the syntheses of (±)-lichesterinic acid (12), (±)-phaseolinic acid (13), (±)-nephromopsinic acid (14), (±)-rocellaric acid (15), and (±)-dihydroprotolichesterinic acid (16).Mahidol UniversityBiochemistry, Genetics and Molecular BiologyChemical EngineeringChemistryPharmacology, Toxicology and PharmaceuticsVicinal dianion of triethyl ethanetricarboxylate: Syntheses of (±)-lichesterinic acid, (±)-phaseolinic acid, (±)-nephromopsinic acid, (±)-rocellaric acid, and (±)-dihydroprotolichesterinic acidArticleSCOPUS10.1002/1522-2675(200211)85:11<3792::AID-HLCA3792>3.0.CO;2-Q