Equilenin
Equilenin, also known as 6,8-didehydroestrone, as well as estra-1,3,5(10),6,8-pentaen-3-ol-17-one, is a naturally occurring steroidal estrogen obtained from the urine of pregnant mares.[2] It was the first complex natural product to be fully synthesized, in work reported by 1940 by Bachmann and Wilds.[3] The synthesis developed by the Bachmann group started from Butenand's ketone[4] – the 7-methoxy structural analog of 1,2,3,4-tetrahydrophenanthren-1-one[5] – and which can be readily prepared from 1,6-Cleve's acid.[3] Nicolaou described this preparation as ending the era preceding the post-World War II work of Robert Burns Woodward that introduced enantioselective synthesis;[4] in this synthesis, a mixture of stereoisomers were prepared and then resolved,[6] and the choice of target was partly because of the existence of only two chiral carbons and hence only four stereoisomers.[5] The overall yield of the synthesis was 2.7% based on a twenty-step process starting from Cleve's acid.
Routes ofadministrationBy mouthDrug classEstrogenIUPAC nameCAS NumberDrugBankChemSpiderChEMBLCompTox DashboardECHA InfoCardFormulaMolar massSMILESnaturally occurringsteroidalpregnantconjugated estrogensBachmannstructural analog1,2,3,4-tetrahydrophenanthren-1-oneCleve's acidClaisen condensationReformatsky reactionArndt–Eistert reactionDieckmann condensationNicolaouRobert Burns Woodwardenantioselective synthesisresolvedBachmann WEWilds ALJ. Am. Chem. Soc.Nicolaou KCAcademic PressEstrogensantiestrogensAlfatradiolandrogensanabolic steroidstestosteronemethyltestosteronemetandienoneprogestinsnorethisteronenoretynodreletynodiol diacetatetiboloneClomestroneCloxestradiol acetateConjugated estriolEpiestriolEpimestrolEsterified estrogensEstetrolEstradiolestradiol acetateestradiol benzoateestradiol cypionateestradiol enanthateestradiol undecylateestradiol valeratepolyestradiol phosphateestradiol ester mixturesClimacteronEstramustine phosphateEstriolestriol succinatepolyestriol phosphateEstrogenic substancesEstroneEstrone sulfateEstropipate (piperazine estrone sulfate)EthinylestradiolEthinylestradiol sulfonateHydroxyestrone diacetateMestranolMethylestradiolMoxestrolNilestriolPrasterone (dehydroepiandrosterone; DHEA)Prasterone enanthatePrasterone sulfatePromestrieneQuinestradolQuinestrolBenzestrolBifluranolChlorotrianiseneDienestrolDienestrol diacetateDiethylstilbestrol (stilbestrol)Dimestrol (diethylstilbestrol dimethyl ether)Fosfestrol (diethylstilbestrol diphosphate)Mestilbol (diethylstilbestrol monomethyl ether)Doisynoestrol (fenocycline)HexestrolMethallenestrilMethestrol (promethestrol)Methestrol dipropionate (promethestrol dipropionate)ParoxypropioneQuadrosilanTriphenylbromoethyleneTriphenylchloroethyleneZeranolProgonadotropinsAntiandrogensbicalutamideGnRH agonistsGnRH (gonadorelin)leuprorelinGonadotropinsAcolbifeneAnordrinBazedoxifeneBroparestrolClomifeneCyclofenilEnclomifeneEpitiostanolLasofoxifeneMepitiostaneOrmeloxifeneOspemifeneRaloxifeneTamoxifen