Synthesis of Organotin Substituted Tricyclic Macrodiolides
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...
| Autores: | , , , |
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| Tipo de documento: | artigo |
| Estado: | Versão publicada |
| Data de publicação: | 2015 |
| País: | Argentina |
| Recursos: | Consejo Nacional de Investigaciones Científicas y Técnicas |
| Repositório: | CONICET Digital (CONICET) |
| Idioma: | inglês |
| OAI Identifier: | oai:ri.conicet.gov.ar:11336/4656 |
| Acesso em linha: | http://hdl.handle.net/11336/4656 |
| Access Level: | Acceso aberto |
| Palavra-chave: | ORGANOTIN SUBSTITUED MACRODIOLIDES CYCLOHYDROSTANNATION STEREOSELECTIVE TANDEM CYCLIZATION https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| Resumo: | 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. |
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