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1、MAGNETICRESONANCEINCHEMISTRY,VOL.30,500-506(1992)SpectroscopicAnalysisof3~-Acetoxy-8-hydroxy-8,1l-epoxy-8,9-seco-6,1l-cyclolanostane-7,9-dioneFredY.Fujiwara,VeraG.RehderandAnitaJ.Marsaioli*IstitutodeQuímicadaUniversidadeEstadualdeCampinas,C.P.6154,Campinas13081SP,BrazilSpectroscopica
2、nalysisofaianostanederivative,whichwassynthesizedwithaviewtoitsappiicationasaninterme-diateinchiralbuildingblocksyntheses,ispresentedtogetherwiththeconformationalanalysisofasecolanostane-7-8-9,ll-tetraone.KEYWDRDS3~-Acetoxy-8-hydroxy-8,9-epoxy-8,9-Seco-6,1l-cyclolanostane-7,9-dione,3
3、~-Acetoxy-8,9-secolanostane-7,8,9,11-tetraone.13CNMRMM2molecularmechanicscalculations.Conformationalanalysis2DNMR.withtheirconformationsandreactivity.'Thetetra-INTRODUCTIONketone1anditscycloderivative2wereparticularlyinterestingbecauseoftheirnovelstructures(Scheme2),3Inrecentyears,co
4、nsiderableresearchefforthasbeenand2revealedgoodantithromboticactivityfocusedonthesynthesisofchiralbuildingblocks.'The(pharmacologicalactivitytestswererunatSANOFIinterestinthesechiralcarbonfragmentsstemsfromtheRecherche,CentredeMontpellier,Montepellier,everincreasingdemandforenantiome
5、ricaliypurecom-France).Inthispaperwepresenttheassignmentofthepounds.Withaviewtoeasyaccesstopolyfunctiona-'HandI3CNMRof31(-acetoxy-8-hydroxy-8,11-lizedcyclopentaneandcyclohexanechiralbuildingepoxy-8,9-seco-6,1l-cyclolanostane-7,9-dione(2),usingblockswehavesynthesizedsevera18,9-secolan
6、ostanes2Dexperiments(lHxI3CCORR,'Hx'3C-COLOCwhich,onoxidatecleavage,leadtofragmentswithand'Hx'Hdoublequantumfilteredphasesensitive12-18carbonatoms(Scheme1).Whiledevelopingthis(COSYexperiments).Inconnectionwiththesynthesisprogrammewebecameawarethatalthoughseco-of2wehadtoundertakemolec
7、ularmechanicscalcu-lanostanederivativeshavebeenknownforyears,lationsof3~-acetoxy-8,9-secolanostane-7,8,9,11-tetra-nothinghasbeenpublishedconcerningtheirspectro-one(1)inordertogainaninsightintoitsvariousscopicanalysis.Wethereforedecidedtostudy8,9-seco-conformationsandrelatedreactiviti
8、es.and8,9-se
