天然產物siphonazole和stereocalpina的合成研究

1、合肥工業(yè)大學碩士學位論文天然產物Siphonazole和StereocalpinA的合成研究姓名：朱玉川申請學位級別：碩士專業(yè)：生物化工指導教師：馮乙巳20080501TotalSynthesisofNaturalProductStereocalpinAABSTRACTSiphonazoleandRetrosyntheticanalysisandstudyonChemicalssynthesisofnaturalproductSipho

2、nazoleandStereocalpinA，whichweredescribedinthispaper，ThesynthesisrouteofSiphonazolestartwithLThrOMeHClandDichlorocyanogentoobtainOxadiazolineintermediateundertheCatalyticofsodiummethoxideThecompound14werepreparedthrought

3、heprocessingofeliminationreactions、acidcatalysisandsubstitutionreactionsThen，Wittigreagentwassynthesisfromcompound14andtriphenylphosphine，thencompound17wasobtainfromTBSvanillinandWittigreagentundertheWittigSchlosserreact

4、ionsintheoveryield44％Aldehydewasobtainedaftercompound17OxidationReactions，andmixtedwiththecompound14toformCCbondviaReformatskyreactionsTheproductwashydrolysisandcouplingwithcompound114assistedbythecouplingreagentsBOPCIAf

5、terremovingtheTBSprotectinggrouptoaffordthenaturalproductofSiphonazoleinanoveryield8％Theimportantcompound25and210oftheStereocalpinAwerecompletedThecouplingwitheachotherandringclosurewasinworkingprogressThesynthesisrouteo

6、fthecompound25startwithDPheviaReductionreactins(NaBH4／12)andcyclizationwithtriphosgeneunderthealkalineconditiontoaffordEvanschiralauxiliaryThenthroughcondensationreactions、Alkylahonreactionsintheoveryield31％Theothercompo

7、und210wasbeginningwithLPheO‘BuItreductionbyNaBH4afterLPheO‘Buformationiminewithbenzaldehydeandformaldehyde，andfollowedbyremovingoftheBngroupwithcatalytichydrogenolysis，thencouplingwithCbz—LPheviaBOPCIintheoveryield59％Key