Pallambins-C-and-D的11步全合成Phil-S.-Baran.pptx

Retrosynthetic Analysis;Total Synthesis of Pallambins C and D ;Reagents and conditions: (1) furfuryl alcohol (1 equiv), 1,1-dimethoxy-N,N-dimethylpropan-1-amine (1.5 equiv), PhMe, 110 °C then TMDS (2equiv), Ti(OiPr)4 (1.5 equiv), 50 °C (75%, one-pot); (2) ethyl vinyl ketone (1.5 equiv), Bu4NBr (10 mol %), 60% aq. KOH, PhMe, 23 °C (68%);Eschenmoser-Claisen rearrangement;Total Synthesis of Pallambins C and D ;Reduction of the resulting amide;Total Synthesis of Pallambins C and D ;Robinson annulation ;Evolution of synthetic strategy to enone 6;Evolution of synthetic strategy to enone 6;Total Synthesis of Pallambins C and D ;Photooxygenation of heterocycles, Iesce, M. R.; Cermola, F.; Temussi, F. Curr. Org. Chem. 2005, 9,109 ;Total Synthesis of Pallambins C and D ;Mukaiyama aldol reaction ;;Evolution of [3.2.1] bicycle construction and C8 diastereoselectivity;Evolution of [3.2.1] bicycle construction and C8 diastereoselectivity;Total Synthesis of Pallambins C and D ;A mechanistic model for C-ring formation ;Total Synthesis of Pallambins C and D ;Cleavage of ethers with acyl halides ;Evolution of C9-C11 reduction;Evolution of C9-C11 reduction;Evolution of C9-C11 reduction;Evolution of C9-C11 reduction;Evolution of C9-C11 reduction;Evolution of C9-C11 reduction;Total Synthesis of Pallambins C and D ;Cyclization 4 ;Cyclization 4 ;Total Synthesis of Pallambins C and D ;Evolution of γ-lactone construction;Evolution of γ-lactone construction;Prvost Reaction;Evolution of γ-lactone construction;Sakurai Allylation Reaction ;Total Synthesis of Pallambins C and D ;Conclusion;Thanks for your attention;Reagents and conditions