Double conjugate addition of a nitropropionate ester to a quinone monoketal: synthesis of an advanced intermediate to (+/-)-gelsemine.
A double conjugate addition between the lithium dianion of ethyl 3-nitropropionate and p-benzoquinone dimethyl ketal afforded a mixture of diastereomeric [3.2.1]bicylooctanones. These products were converted into an advanced intermediate previously carried forward to (+/-)-gelsemine by Fukuyama and Liu.
Grecian
Scott
S
Department of Medicinal Chemistry, 1251 Wescoe Hall Drive, Room 4070, Malott Hall, The University of Kansas, Lawrence, Kansas 66045-7582, USA.
Aubé
Jeffrey
J
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D016227:Benzoquinones / Q000737:chemistry; D008094:Lithium / Q000737:chemistry; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D011422:Propionates / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D016227:Benzoquinones; D009574:Nitro Compounds; D011422:Propionates; C522209:ethyl 3-nitropropionate; C004532:quinone; C063230:gelsemine; D008094:Lithium