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Garnsey, Michelle R.,Slutskyy, Yuriy,Jamison, Christopher R.,Zhao, Peng,Lee, Juyeol,Rhee, Young Ho,Overman, Larry E. American Chemical Society 2018 Journal of organic chemistry Vol.83 No.13
<P>The development of a convergent fragment coupling strategy for the enantioselective total syntheses of a group of rearranged spongian diterpenoids that harbor the <I>cis</I>-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.</P> [FIG OMISSION]</BR>