Total Synthesis of (-)-Cocaine and (-)-Ferruginine
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Total synthesis of (-)-cocaine and (-)-ferruginine. Cheng G , Wang X , Zhu R , Shao C , Xu J , Hu Y . Source Department of Chemistry, Tsinghua University, Beijing 100084, People's Republic of China. Abstract Total synthesis of tropane alkaloids (-)-cocaine and (-)- ferruginine were accomplished in nine steps each and in 55% and 46% overall yields, respectively, starting from the known Betti base derivative (+)-(7aR,10R,12S)-10-(1H-benzotriazol-1-yl)- 7a,8,9,10-tetrahydro-12-phenyl-12H-naphtho[1,2-e]pyrrolo[2,1-b] [1,3]oxazine. In this novel route, RCM reaction and 1,3-dipolar cycloaddition were employed as key steps for the enantioselective construction of tropane skeleton and the regioselective introduction of 3-bromo-2-isoxazoline ring as masked cis-2,3-disubstituents. To obtain the desired precursor (2S,5R)-2-allyl-5-vinylpyrrolidine for RCM reaction, we developed a general and practical method for the preparation of enantiopure cis-2,5-disubstituted pyrrolidines bearing alkene- and/or alkyne-containing substituents. We also offered two highly efficient pathways for the conversion of the 3-bromo-2- isoxazoline ring into the desired cis-2,3-disubstituted groups in (-)-cocaine and (-)-ferruginine. PMID: 21391709 [PubMed - indexed for MEDLINE] Publication Types, MeSH Terms, Substances Publication Types Research Support, Non-U.S. Gov't MeSH Terms
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Transcript of Total Synthesis of (-)-Cocaine and (-)-Ferruginine
Total synthesis of (-)-cocaine and (-)-ferruginine.Cheng G, Wang X, Zhu R, Shao C, Xu J, Hu Y.SourceDepartment of Chemistry, Tsinghua Uniersity, !ei"ing #$$$%&, 'eop(e)s Repu*(i+ of China.AbstractTota( synthesis of tropane a(,a(oi-s ./0/+o+aine an- ./0/ferruginine 1ere a++omp(ishe- in nine steps ea+h an- in 223 an- &43 oera(( yie(-s, respe+tie(y, starting from the ,no1n !etti *ase -eriatie .50/.6aR,#$R,#7S0/#$/.#H/*en8otria8o(/#/y(0/6a,%,9,#$/tetrahy-ro/#7/pheny(/#7H/naphtho:#,7/e;pyrro(o:7,#/*;:#,n this noe( route, RC? rea+tion an- #, P Citerature P 'u*?e-Write to the He(p Des, Simple *'%+ &irectory ,etting Started DC!> B-u+ation DC!> He(p ?anua( DC!> Han-*oo, Training G Tutoria(s )esources Chemi+a(s G !ioassays Data G Soft1are DDE G RDE Domains G Stru+tures Genes G B=pression Geneti+s G ?e-i+ine Genomes G ?aps Homo(ogy Citerature 'roteins SeLuen+e Ena(ysis Ta=onomy Training G Tutoria(s Hariation Popular 'u*?e- Du+(eoti-e !CEST 'u*?e- Centra( Gene !oo,she(f 'rotein I?>? Genome SD' Stru+ture #eatured Geneti+ Testing Registry 'u*?e- Hea(th Gen!an, Referen+e SeLuen+es ?ap Hie1er Human Genome ?ouse Genome >nf(uen8a Hirus 'rimer/!CEST SeLuen+e Rea- Er+hie *'%+ +nformation E*out DC!> Resear+h at DC!> DC!> De1s(etter DC!> KT' Site DC!> on Ka+e*oo, DC!> on T1itter DC!> on YouTu*eB=terna( (in,. '(ease reie1 our pria+y po(i+y. DC? D>H DHHS USE.go Copyright Q Dis+(aimer Q 'ria+y Q E++essi*i(ity Q Conta+t Datio
