Synthesis of Organotin Substituted Tricyclic Macrodiolides

• Autor(a) principal: Zacconi,Flavia C.
• Data de Publicação: 2016
• Outros Autores: Ocampo,Romina A., Podestá,Julio C., Koll,Liliana C.
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Journal of the Brazilian Chemical Society (Online)
• Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016000300484
• topic: organotin substituted macrodiolides; cyclohydrostannation; stereoselective tandem cyclization

The radical addition of triorganotin hydrides, R3SnH (R =n-butyl, phenyl, neophyltin), to four unsaturated diesters of (11R,12R)-9,10-dihydro-9,10-ethaneanthracene-11,12-dimethanol leads to products of cyclohydrostannation with an average yield of around 80%. Whereas the addition of these hydrides to diacrylate and dimethacrylate leads to the expected mixtures containing two and four distereoisomeric cyclized products respectively, the addition to di-2-methyl- and di-2-phenylcinnamate yields only four out of the sixteen possible stereoisomers. The observed high stereoselectivity is consistent with a radical tandem cyclohydrostannation mechanism. Full proton (1H), carbon 13 (13C) and tin 119 (119Sn) nuclear magnetic resonance (NMR) data are given.