| Autor: |
Garnsey MR; Department of Chemistry , University of California , Irvine , California 92697-2025 , United States., Slutskyy Y; Department of Chemistry , University of California , Irvine , California 92697-2025 , United States., Jamison CR; Department of Chemistry , University of California , Irvine , California 92697-2025 , United States., Zhao P; Department of Chemistry , University of California , Irvine , California 92697-2025 , United States., Lee J; Department of Chemistry , University of California , 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 , California 92697-2025 , United States. |
| Abstrakt: |
The development of a convergent fragment coupling strategy for the enantioselective total syntheses of a group of rearranged spongian diterpenoids that harbor the cis-2,8-dioxabicyclo[3.3.0]octan-3-one unit is described. The key bond disconnection relies on a late-stage fragment coupling between a tertiary carbon radical and an electron-deficient alkene to unite two ring systems and form two new stereocenters, one of which is quaternary, in a stereoselective and efficient manner. This strategy is applied toward scalable 14-15 step syntheses of three rearranged spongian diterpenoids, cheloviolenes A and B, and dendrillolide C. |
