%0 Journal Article %A Trost, Barry M. %A Ashfeld, Brandon L. %D 2008 %T Coupling of Alkenes and Alkynes: Synthesis of the C1−C11 and C18−C28 Fragments of Miyakolide %U https://acs.figshare.com/articles/journal_contribution/Coupling_of_Alkenes_and_Alkynes_Synthesis_of_the_C1_C11_and_C18_C28_Fragments_of_Miyakolide/2939032 %R 10.1021/ol800347u.s001 %2 https://ndownloader.figshare.com/files/4637719 %K ring fragment %K D rings %K D ring pyran %X A transition metal-mediated, atom-economical approach toward the crucial A and D rings of miyakolide is described. A Pd-catalyzed alkyne−alkyne coupling/6-endo-dig cyclization is employed to assemble the A ring fragment. The key D ring pyran is constructed utilizing an Ru-catalyzed alkene−alkyne coupling followed by a Pd-catalyzed allylic alkylation to establish the all-cis stereochemistry. %I ACS Publications