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Total synthesis of (+)-acutiphycin.
J Org Chem ; 72(25): 9736-45, 2007 Dec 07.
Artigo em Inglês | MEDLINE | ID: mdl-17985925
ABSTRACT
Synthetic studies toward the total synthesis of (+)-acutiphycin (1) resulted in the discovery of additive-free, highly regioselective nickel-catalyzed reductive coupling reactions of aldehydes and 1,6-enynes and the construction of an advanced intermediate in studies directed toward the synthesis of 1. Ultimately, although not employing the nickel-catalyzed reaction, a highly convergent total synthesis of (+)-acutiphycin featuring an intermolecular SmI2-mediated Reformatsky coupling reaction and macrolactonization initiated by a retro-ene reaction of an alkoxyalkyne was achieved. The resulting synthesis was 18 steps in the longest linear sequence from either methyl acetoacetate or isobutyraldehyde.
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Coleções: Bases de dados internacionais Base de dados: MEDLINE Assunto principal: Macrolídeos / Compostos Heterocíclicos Idioma: Inglês Revista: J Org Chem Ano de publicação: 2007 Tipo de documento: Artigo País de afiliação: Estados Unidos