Filip Petronijevic Current Literature Presentation April, 24 th 2010.
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1 Filip Petronijevic Current Literature Presentation April, 24 th Total Synthesis of ()-mplanadine A Using an Iridium-Catalyzed Pyridine C- Functionalization Daniel F. Fischer and Richmond Sarpong J. Amer. Chem. Soc., ASAP 2' mplanadine A Synthesis of ()-mplanadine A, an Inducer of erutrophic Factor Excretion Changxia Yuan, Chih-Tsung Chang, Abram Axelrod, and Dionicio Siegel J. Amer. Chem. Soc., ASAP Filip Wipf Group Page 1 of 14 4/26/2010
2 Lycopodium Alcaloids and mplanadine A C A 8 D 7 5 Lycopodine Fawcettimine Lycodine Phlegmarine 2' mplanadine A For review see: udlicky, T.; and Reed, J.W. In The Way of Synthesis, 1st ed.; Wiley-VC, 2007; pp nroy,. J. Tetrahedron Lett. 1960, 10, 4. Fisher, D.; Sarpong, R.J. Amer. Chem. Soc. ASAP. Filip Wipf Group Page 2 of 14 4/26/2010
3 ow Does ature Make mplanadine A: iosynthesis of Lycopodium Alcaloids 2 2 Lys (K) C 2 -C cadaverine diamine oxidase 2 malonyl A X X -C 2 oxidative dimerization -C 2 X pelletierine oxidation dimerization lycodine complanadine A udlicky, T.; Reed, J.W. In The Way of Synthesis, 1st ed.; Wiley-VC, 2007; pp and references therein. nroy,. J. Tetrahedron Lett. 1960, 10, 4. Stork, G. Pure Appl. Chem. 1968, 17, 8. Filip Wipf Group Page of 14 4/26/2010
4 Retrosynthetic Approaches in the Sarpnog and Siegel Groups oc Tf oc oc Tf oc Sarpong's group complanadine A R' R Si 4 R' Siegel's group R' R Si SiR R' Yuan, C.; Chang, C.-T.; Axelrod, A.; Siegel, D. J. Amer. Chem. Soc. ASAP. Fisher, D.; Sarpong, R.J. Amer. Chem. Soc. ASAP. Filip Wipf Group Page 4 of 14 4/26/2010
5 The Key Step in Siegel s Synthesis: [222] Cycloaddition L 2 (L = C, PR, olefin) L enzene and Pyridine Synthesis by Cyclotrimerization 1 L 2 L "" 2 2 C R R "" 9 10 R R or R C 7 C 8 R For an excelent review on pyridine synthesis by metal diated cyclotrimerization, see: Varela, J.A.; Saá, C. Chem. Rev. 200, 10, 787. Funk. R.L.; Volhardt, K.P.C. J. Amer. Chem. Soc. 1980, 102, 525. Filip Wipf Group Page 5 of 14 4/26/2010
6 The Key Step in Sarpong s Synthesis: Suzuki Reaction R 1 -R 2 L n Pd reductive elimination L R 2 -X oxidative addition L n Pd R 1 R 2 R transmetallation R R 2 L R 1 R R 2 R 1 R 2 M R - L n Pd X R 2 M R - L n Pd R R 2 M X - Kurti, L.; Czako,.In Strategic Applications of amed Reactions in rganic Synthesis; Elsevier Academic Press: urlington, MA, 2005; pp Filip Wipf Group Page 6 of 14 4/26/2010
7 Sarpong: Precursors Syntheses C aet Et 0 C to rt C p-ts 150 C 5% C Zn( ) 2 acetone oxime 2, 90 C 120 C vacuum 5% 2 0% 2 2 PhS, tama MTE, reflux 1. a, Ac 40 C quantitative Li, 0 C 94% (trans/cis 66:4) 7% (trans/cis 40:60) SPh 1. (C 2 ) 2, 2. CaC, 80 C 52% 1. I 2, pyr. DCM, 95% 2. AI, TT acrylonitrile Ph, 70% 2 2. LiAl 4, Et 2 0 C, 90% äslund, G.; Senning, A.; Lawesson, S.-. Act. Chem. Scand. 1962, 16, 124. Koylovich, M..; Kukushkin, V.Y.; aukka, M.; Fransto da Silu, J.J.R.; Pombeiro, A.J.L. Inorg. Chem. 2002, 41, Liu, K.-M.; Sha, C.-K. Chem. mmun. 2008, 1, 91. Schyster, E.; Jas, G.; Schumann, D. rg. Prep. Proc. Int , 24, 670. Fisher, D.; Sarpong, R.J. Amer. Chem. Soc. ASAP. Filip Wipf Group Page 7 of 14 4/26/2010
8 Sarpong: Tricyclic Intermediate Synthesis 70% Cl 4 dioxane 105 C, 20 h 2 2 then oc 2, Et TF, 60 C 65% oc Schyster, E.; Jas, G.; Schumann, D. rg. Prep. Proc. Int , 24, 670. Fisher, D.; Sarpong, R.J. Amer. Chem. Soc. ASAP. Filip Wipf Group Page 8 of 14 4/26/2010
9 Sarpong s Synthesis: mplanadine A Formation oc Pb(Ac) 4 CCl, rt 84% oc Tf 2, pyridine -78 C to rt 72% oc Tf Tf oc cat. Pd(Ac) 2 dppf, C 2 4 Et, 60 C 90% oc cat. [Ir(CD)()] 2 dtu-dipy [(pin)] 2 TF, 80 C 75% oc oc tu Tf oc 1. PdCl 2 (dppf), K P Cl, 70 C 42% (over 2 steps) mplanadine A 2' tu dtu-dipy [(pin)] 2 tu tu Ir CE pin pin pin Takagi, J.; Sato, K.; artwig, J.F.; Ishiyama, T.; Miyaura,. Tetrahedron Lett. 2002, 4, Ishiyama, T.; Miyaura,. Pure Appl. Chem. 2006, 78, 169. Cho, J.-Y.; Tse, M.K.; olmes, D.; Maleczka, R.E.; Smith III, M.R. Science 2002, 295, 05. Ishiyama, T.; Takagi, J.; Ishida, K.; Miyaura,.; Anastasi,.R.; artwig, J.F. J. Amer. Chem. Soc. 2002, 124, 90. Fisher, D.; Sarpong, R.J. Amer. Chem. Soc. ASAP. Filip Wipf Group Page 9 of 14 4/26/2010
10 Siegel s Synthesis: Starting Material Preparation SPh 1. a, I(C 2) Ac DMF, 2 C, 6% Ac 1. a) C 2 C, n-uli b) ethyl salicilate, Et 2-78 C Ac 2. m-cpa, C 2 Cl 2-78 to 2 C, 77% 2. CsF, C C, 2 C 45% (over 2 steps) C 1. CCMgCl, TF 2 C, 97% 2. Ac 2, Mg(Cl 4 ) 2 2 C, 97%. PhC 2 2, CuCl TF, 66 C, 92% Ph C Ac 1. K 2 C, 2 C, 99% 2. PPh, imidazole CCl 4, 77 C, 75% Cl C C C Yuan, C.; Chang, C.-T.; Axelrod, A.; Siegel, D. J. Amer. Chem. Soc. ASAP Filip Wipf Group Page 10 of 14 4/26/2010
11 Siegel s Synthesis: Cyclotrimerization and Regioselectivity Problem C (C) 2 TF, 140 C 82% 25:1 1. TAF, TF 66 C, 85% 2. LiMDS, Cl TF, 2 C, 90% (C) 2 TF, 140 C 82% Yuan, C.; Chang, C.-T.; Axelrod, A.; Siegel, D. J. Amer. Chem. Soc. ASAP Filip Wipf Group Page 11 of 14 4/26/2010
12 Siegel s Synthesis: End Game Changing the regioselectivity: C C (C) 2 dioxane, 140 C C A A : =. : 1 (47% yield) with 8 equiv. PPh A : = 1 : (56% yield) C C 1. TAF, dioxane 101 C, 99% 2. Pd/C, 2, 2 C, 78%. Cl, 50 C, 90% The use of formyl in place of the benzyl group was required as coupling partners failed to react The ability of PPh to change the regioselectivity warrants furhter study Yuan, C.; Chang, C.-T.; Axelrod, A.; Siegel, D. J. Amer. Chem. Soc. ASAP Filip Wipf Group Page 12 of 14 4/26/2010
13 Siegel s Synthesis: Cyclotrimerization Regioselectivity Explanation LUM ~ 0.5 hartree route 1 ~ 0.4 hartree route 2 prefered biggest lobe of diyne's LUM ß to the metal Si Si Si Si Ab initio energies: prefered Varela, J.A.; Castedo, L.; Saá, C. J. Amer. Chem. Soc. 1998, 120, Stockis, A.; offmann, R. j. Amer. Chem. Soc. 1980, 102, Filip Wipf Group Page 1 of 14 4/26/2010
14 nclusions oth syntheses are based on the symmetry of mplanadine A: ature mimicking approaches Sarpong s key step: artwig-miyaura Ir(I)-catalyzed borylation and Suzuki -Miyaura coupling oc Siegel s key step: (I)-catalyzed [222] cycloaddition cyclotrimerization Tf oc R Si SiR R' R' iological studies in progress: The influence of the compound on primary cultures of rat glial cells and examining the effects on the biosynthesis of neurotrophin mra Filip Wipf Group Page 14 of 14 4/26/2010
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