Synthesis of the C(1)-C(13) Fragment of Leiodermatolide via Hydrogen-Mediated C-C Bond Formation.
| Autor: | Roane J; Department of Chemistry, University of Texas at Austin Austin, Texas 78712, United States., Wippich J; Department of Chemistry, University of Texas at Austin Austin, Texas 78712, United States., Ramgren SD; Department of Chemistry, University of Texas at Austin Austin, Texas 78712, United States., Krische MJ; Department of Chemistry, University of Texas at Austin Austin, Texas 78712, United States. |
|---|---|
| Jazyk: | angličtina |
| Zdroj: | Organic letters [Org Lett] 2017 Dec 15; Vol. 19 (24), pp. 6634-6637. Date of Electronic Publication: 2017 Nov 23. |
| DOI: | 10.1021/acs.orglett.7b03351 |
| Abstrakt: | The C(1)-C(13) fragment of the antimitotic marine macrolide leiodermatolide is prepared in seven steps via hydrogenative and transfer-hydrogenative reductive C-C couplings. A hydrogen-mediated reductive coupling of acetylene with a Roche-type aldehyde is used to construct C(7)-C(13). A 2-propanol-mediated reductive coupling of allyl acetate with (E)-2-methylbut-2-enal at a low loading of iridium (1 mol %) is used to construct C(1)-C(6), which is converted to an allylsilane using Oestereich's copper-catalyzed allylic substitution of Si-Zn reagents. The union of the C(1)-C(6) and C(7)-C(13) fragments is achieved via stereoselective Sakurai allylation. |
| Databáze: | MEDLINE |
| Externí odkaz: |
|