000059619 001__ 59619
000059619 005__ 20180317092300.0
000059619 0247_ $$2doi$$a10.1002/hlca.19940770103
000059619 022__ $$a0018-019X
000059619 037__ $$aARTICLE
000059619 245__ $$aEnantioselective Synthesis of (-)-Conduramine C-1 and Aminobromocyclitol Derivatives
000059619 260__ $$c1994
000059619 269__ $$a1994
000059619 336__ $$aJournal Articles
000059619 500__ $$aUniv lausanne,chim sect,ch-1005 lausanne,switzerland.
000059619 520__ $$a(1S,2R,6R,7R)-4-Phenyl-3,10-dioxa-5-azatricyclo[5.2.1.0(2,6)]dec-4-en-9- one ((+)-5) obtained in 6 steps from the Diels-Alder adduct of furan to 1-cyanovinyl (1S)-camphanate ((+)-3) was reduced to the corresponding endo-alcohol (-)-6 the treatment of which with HBr/AcOH provided (-)-(3aS,4S,6R,7S,7aR)-4 beta-bromo-3a beta,4,5,6,7,7a beta-hexahydro-2-phenyl-1,3-benzoxazole-6 beta,7 alpha-diyl diacetale ((-)-17). Elimination of HBr with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and acidic hydrolysis furnished (-)-(1R,2S,3R,4R)-4-aminocycrohex-5-ene-1,2,3-triol(= (-)-conduramine C-1; (-)-1).
000059619 6531_ $$aPure 7-oxabicyclo<2.2.1>hept-5-en-2-yl derivatives
000059619 6531_ $$adiels-alder
000059619 6531_ $$areactions
000059619 6531_ $$anitroso-compounds
000059619 6531_ $$adiene synthesis
000059619 6531_ $$apseudo-sugars
000059619 6531_ $$apolyhydroxyamino compounds
000059619 6531_ $$amicrobial oxidation
000059619 6531_ $$acyclitol reactions
000059619 6531_ $$anaked sugars
000059619 6531_ $$aenzymatic asymmetrization
000059619 700__ $$aAllemann, S.
000059619 700__ $$0240222$$aVogel, P.$$g123681
000059619 773__ $$j77$$k1$$q1-9$$tHelvetica Chimica Acta
000059619 909CO $$ooai:infoscience.tind.io:59619$$particle$$pSB
000059619 909C0 $$0252076$$pLGSA$$xU10111
000059619 937__ $$aLGSA-ARTICLE-1994-003
000059619 970__ $$aISI:A1994MW15900001/LGSA
000059619 973__ $$aEPFL$$rREVIEWED$$sPUBLISHED
000059619 980__ $$aARTICLE