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pubmed-article:12137516pubmed:abstractTextTransition metal-catalyzed cycloaddition reactions represent powerful methods for the construction of complex polycyclic systems. We have developed a new intermolecular metal-catalyzed [4 + 2 + 2] cycloaddition of heteroatom-tethered enyne derivatives with 1,3-butadiene. This study demonstrates that excellent selectivity can be obtained for the heterocycloaddition adducts through the judicious choice of silver salt. The development of the tandem rhodium-catalyzed allylic substitution [4 + 2 + 2] cycloaddition provides a convenient three-component coupling that circumvents the prior formation of the enyne derivative. Finally, the introduction of a stereogenic center at C-2 leads to a diastereoselective cycloaddition, which provides a powerful new method for the construction of bicyclic octanoid ring systems applicable to target directed synthesis.lld:pubmed
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pubmed-article:12137516pubmed:authorpubmed-author:BaumErich WEWlld:pubmed
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pubmed-article:12137516pubmed:pagination8782-3lld:pubmed
pubmed-article:12137516pubmed:dateRevised2008-1-17lld:pubmed
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pubmed-article:12137516pubmed:articleTitleIntermolecular transition metal-catalyzed [4 + 2 + 2] cycloaddition reactions: a new approach to the construction of eight-membered rings.lld:pubmed
pubmed-article:12137516pubmed:affiliationDepartment of Chemistry, Indiana University, Bloomington, Indiana 47405, USA. paevans@indiana.edulld:pubmed
pubmed-article:12137516pubmed:publicationTypeJournal Articlelld:pubmed
pubmed-article:12137516pubmed:publicationTypeResearch Support, U.S. Gov't, P.H.S.lld:pubmed
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