孕二烯二酮、3-OHAT、脫氫氯甲睪酮合成研究.pdf

1、華東師范大學碩士學位論文孕二烯二酮、3OHAT、脫氫氯甲睪酮合成研究姓名：于濤申請學位級別：碩士專業(yè)：有機化學指導教師：楊帆湯杰20050401AbstractThiSdissertationisdividedintothreeparts(1)Synthesisofguggulsterones(trans—andcis)4，17(20)一Pregnadiene一3，16一dione)(2)Synthesisof3B～hydroxyand

2、rost一4一en6，17一dione(3OHAT)(3)Synthesisof4chloro17證methylandrostane一17B—ol一3一one(dehydrochloro—methyltestosterone)Guggutsteronesisakindofthyroidstimulatorywhichhaveobviousfunctionalitysuitableforelaborationintoelinicallyu

3、sefulsteroidaldrug。Ithasbeenfoundtopossessdiversebiological／pharmalogicaIactivities。Using16一dehydropregnaloneacetateasstartingmaterial，thetargetcompoundguggulsteronesweresynthesizedthroughfivestepsincludingthereductionwi

4、thKBH4，acid—catalyzedrearrangement，bydrolysiS，Oppenaueroxidationandthermal—chemicalisomerizationThetotalyieldis42％KBH4／CeCl3wasusedasreductionreagentreplacingLiAIH4，WhichreducedthecostandsimplifiedtheexperimentprocessSom

5、estudiesdealwiththeolefinisomerization，anddiverseproportionalcis—andtrans“—isomerizationcanbeobtainedbycontrolingthereactioneonditions3一hydroxyandrost一4一en一6，17一dione(3OHAT)isapowerfulnon—androgeniCaromataseinhibitorItiS

6、veryeffectiveindecreasingtherateoftherecurringofbreastcancerButtherewasn’taroutesuitable：forindustrializationreportedinallthedocument。Inthisdissertation，wesynthesized3OHATusingdehydroepiandrosteronacetatasstartingmateria

7、lthroughfivestepsincludingoxidationbyperformieacid，cleavagedbyperiodicacid，oxidationbyIBX，eliminationandhydrolysiSThetotalyieldiS48％ThisrouteiSofcharacteristicoflowcost，highyieldandeasyoperation，4chloro一17a—methylandrost