Versatile Construction of 6-Substituted cis-2,8-Dioxabicyclo[3.3.0]octan-3-ones: Short Enantioselective Total Syntheses of Cheloviolenes A and B and Dendrillolide C.
| Autor: | Slutskyy Y; Department of Chemistry, University of California, Irvine , Irvine, California 92697-2025, United States., Jamison CR; Department of Chemistry, University of California, Irvine , Irvine, California 92697-2025, United States., Zhao P; Department of Chemistry, University of California, Irvine , Irvine, California 92697-2025, United States., Lee J; Department of Chemistry, University of California, Irvine , Irvine, California 92697-2025, United States., Rhee YH; Department of Chemistry, Pohang University of Science and Technology , Hyoja-dong San 31, Pohang, Kyungbook 790-784, Republic of Korea., Overman LE; Department of Chemistry, University of California, Irvine , Irvine, California 92697-2025, United States. |
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| Jazyk: | angličtina |
| Zdroj: | Journal of the American Chemical Society [J Am Chem Soc] 2017 May 31; Vol. 139 (21), pp. 7192-7195. Date of Electronic Publication: 2017 May 22. |
| DOI: | 10.1021/jacs.7b04265 |
| Abstrakt: | A short enantioselective synthesis of 6-substituted cis-2,8-dioxabicyclo[3.3.0]octan-3-ones is described. The pivotal step is coupling of a tertiary radical generated directly from a tertiary alcohol with a 3-chloro-5-alkoxybutenolide. This strategy is applied toward scalable 14-15 step syntheses of three rearranged spongian diterpenoids: cheloviolenes A and B and dendrillolide C. |
| Databáze: | MEDLINE |
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