Synthesis of Organotin Substituted Tricyclic Macrodiolides

ZACCONI, F. C.; OCAMPO, R. A.; PODESTÁ, J. C.; KOLL, L. C

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY

SOC BRASILEIRA QUIMICA

Lugar: San Pablo; Año: 2015 vol. 26 p. 1 - 9

0103-5053

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.