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Catalytic Enantioselective Dihalogenation and the Selective Synthesis of (-)-Deschloromytilipin A and (-)-Danicalipin A.
Landry, Matthew L; Hu, Dennis X; McKenna, Grace M; Burns, Noah Z.
Afiliação
  • Landry ML; Department of Chemistry, Stanford University , Stanford, California 94305, United States.
  • Hu DX; Department of Chemistry, Stanford University , Stanford, California 94305, United States.
  • McKenna GM; Department of Chemistry, Stanford University , Stanford, California 94305, United States.
  • Burns NZ; Department of Chemistry, Stanford University , Stanford, California 94305, United States.
J Am Chem Soc ; 138(15): 5150-8, 2016 Apr 20.
Article em En | MEDLINE | ID: mdl-27018981
A titanium-based catalytic enantioselective dichlorination of simple allylic alcohols is described. This dichlorination reaction provides stereoselective access to all common dichloroalcohol building blocks used in syntheses of chlorosulfolipid natural products. An enantioselective synthesis of ent-(-)-deschloromytilipin A and a concise, eight-step synthesis of ent-(-)-danicalipin A are executed and employ the dichlorination reaction as the first step. Extension of this system to enantioselective dibromination and its use in the synthesis of pentabromide stereoarrays relevant to bromosulfolipids is reported. The described dichlorination and dibromination reactions are capable of exerting diastereocontrol in complex settings allowing X-ray crystal structure analysis of natural and unnatural diastereomers of polyhalogenated stereohexads.
Assuntos

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Hidrocarbonetos Clorados / Lipídeos Idioma: En Revista: J Am Chem Soc Ano de publicação: 2016 Tipo de documento: Article País de afiliação: Estados Unidos

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Hidrocarbonetos Clorados / Lipídeos Idioma: En Revista: J Am Chem Soc Ano de publicação: 2016 Tipo de documento: Article País de afiliação: Estados Unidos