Trifluoromethyl steroids la,b; 2a,b; 3a,b have been synthesized by starting from estren 3,17-dicarbonyl-3,3-dimethyl ether (4) and dl-18-methyl-2(3)l5(10)-estra-diene-17-carbonyl-3-methyl ether (5),and by using trimth...Trifluoromethyl steroids la,b; 2a,b; 3a,b have been synthesized by starting from estren 3,17-dicarbonyl-3,3-dimethyl ether (4) and dl-18-methyl-2(3)l5(10)-estra-diene-17-carbonyl-3-methyl ether (5),and by using trimthyltrifluoromethylsilane as the trifluoromethylating agent under the catalysis of tetrarnethylam-monium fluoride.The overall yields were 82%,76%; 54%,62%; and 27%,25%,respectively The α-configura tion of trifluoromethyl group of 17-position was determined by X-ray crystal diffraction method Compounds 1a,2a and 3a showed high affinity for rat uterus PRc.The test of biological activities of compounds 1b,2b and 3b is proceeding.展开更多
A-nor-Δ3(5),9(10)-estradiene-2,17-dione 1,a potential precursor for synthesis of some new steroidalcontraceptives,was synthesized from 3β-hydroxy-5α-chloro-6β,19-epoxy-androstane-17-one 6 as the sterting mater al,...A-nor-Δ3(5),9(10)-estradiene-2,17-dione 1,a potential precursor for synthesis of some new steroidalcontraceptives,was synthesized from 3β-hydroxy-5α-chloro-6β,19-epoxy-androstane-17-one 6 as the sterting mater al,which is the key intermediate of steroidal contraceptive of norethindrone,in an overall yield of 25% in 5 steps through the sequence of 5 reactions:(i) oxidative dccyclization,(ii) decarhoxylative cyclization,(iii) reductive decy clization,(iv) dehydroxy methylation,(v) deacetoxylation展开更多
DL-norgestrel is a widely used oral contraceptive. D-norgestrel （1） has been synthesized from an optically active intermediate （3） which was prepared from 13-ethyl-8, 14-seco steroid （2） by microbiological asymm...DL-norgestrel is a widely used oral contraceptive. D-norgestrel （1） has been synthesized from an optically active intermediate （3） which was prepared from 13-ethyl-8, 14-seco steroid （2） by microbiological asymmetric reduction(1)Optically active compound （6） or （9） is also an intermediate for the synthesis of D-norgestrel. Thus, com-展开更多
文摘Trifluoromethyl steroids la,b; 2a,b; 3a,b have been synthesized by starting from estren 3,17-dicarbonyl-3,3-dimethyl ether (4) and dl-18-methyl-2(3)l5(10)-estra-diene-17-carbonyl-3-methyl ether (5),and by using trimthyltrifluoromethylsilane as the trifluoromethylating agent under the catalysis of tetrarnethylam-monium fluoride.The overall yields were 82%,76%; 54%,62%; and 27%,25%,respectively The α-configura tion of trifluoromethyl group of 17-position was determined by X-ray crystal diffraction method Compounds 1a,2a and 3a showed high affinity for rat uterus PRc.The test of biological activities of compounds 1b,2b and 3b is proceeding.
基金Project supported by the National Committee for Planned ParenthoodNational Laboratory of Contraceptives+1 种基金Devices ResearchShanghai Institute of Planned Parenthood Research
文摘A-nor-Δ3(5),9(10)-estradiene-2,17-dione 1,a potential precursor for synthesis of some new steroidalcontraceptives,was synthesized from 3β-hydroxy-5α-chloro-6β,19-epoxy-androstane-17-one 6 as the sterting mater al,which is the key intermediate of steroidal contraceptive of norethindrone,in an overall yield of 25% in 5 steps through the sequence of 5 reactions:(i) oxidative dccyclization,(ii) decarhoxylative cyclization,(iii) reductive decy clization,(iv) dehydroxy methylation,(v) deacetoxylation
文摘DL-norgestrel is a widely used oral contraceptive. D-norgestrel （1） has been synthesized from an optically active intermediate （3） which was prepared from 13-ethyl-8, 14-seco steroid （2） by microbiological asymmetric reduction(1)Optically active compound （6） or （9） is also an intermediate for the synthesis of D-norgestrel. Thus, com-
