Total Synthesis of the Sesquiterpenoid Periconianone A Based on a Postulated Biogenesis
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1 Total Synthesis of the Sesquiterpenoid Periconianone A Based on a Postulated Biogenesis C 3 C3 Liffert, R., Linden, A., Gademann, K. J. Am. Chem. Soc. 2017, 139, Presented by: Brendyn Smith CEM 852 April 6 th,
2 Biological interest Isolated from endophyticfungus Periconia sp. Neural anti-inflammatory activity as potential for treating chronic heart failure Periconianone and simpler analogues demonstrated that they can reduce inflammatory biomarkers in inflamed cells C 3 C3 Periconia sp. 2
3 Biomimetic inspired retrosynthesis C 3 biosynthetic hypothesis aldol chemistry R C 3 C3 C3 Key synthetic considerations: -late stage aldol (minimizing side-product(s); quiz at the end) R C 3 Key intermediate for biomimetic strategy -ease of access to α-diazo intermediate 1 C3 -how to access stereochemistry in compound 2 via Rh - insertion/ [3,3]-sigmatropic rearrangement strategy N 2 TBS
4 Quick starting material prep from (R)-carvone FeCl 3 (1.5 mol%) MeMgBr (1.2 equiv.) TMSCl (1.2 equiv.) TMS PhN (2.4 equiv.) Ac (2.4 equiv.) DCM Et 2, -20 C, quant.* Kharasch reaction -78 C to rt 60% vinylogous Mukaiyama aldol *This example used a carvone analogue with a reduced isoprenyl group: Ceccarelli, S. M., Piarulli, U., & Gennari, C., 2001, Tetrahedron, 57(40), Krafft, M. E., & olton, R. A., J. Am. Chem. Soc. 1984, 106, Tian, G. Q., Yang, J., & Rosa-Perez, K., rg. Lett., 2010, 12 (21), pp
5 Setting the stage with some familiar (and unfamiliar) transformations TBSCl (2.0 equiv.) imidazole (3.0 equiv.) DMAP (0.25 equiv.) DCM, rt, 3 h 66% TBS LiCl (0.2 equiv.) CuI (0.1 equiv.) MeMgBr (1.2 equiv.) TMSCl (1.1 equiv.) TF, -40 C, 30 min quant., dr >10:1 TMS TBS TMS N TMS Li LMDS BF 3 Et 2 (1.2 equiv) i-pr (3.0 equiv.) (2.0 equiv.) MeN 2 (3.0 equiv.) DCM, -65 C, overnight 66% dr >10:1 TBS Criegee fragmentation 3, Sudan III (spatula tip) Me/DCM 1:2, -78 C then Cu(Ac) 2 (2.0 equiv.) FeS 4 (1.2 equiv.) -20 C to rt, overnight 67% TBS N N Sudan III N N N Ph N 1. 2 (1 atm) Pd/C (2.5 mol%) EtAc, rt, 2 h LMDS (1.3 equiv.) imidazole NMe 2 2. NaMe, Me, rt, 4 h 88% over 2 steps Robinson annulation TBS F 3 C CF 3 (1.4 equiv.) TF, -78 C, 1.5 h quant. CF 3 TBS N DMAP 5
6 Criegee fragmentation mechanism ozonolysis in Me Me Cu(Ac) 2, FeS 4 Me TBS TBS TBS Me TBS TBS Schreiber, S. L., J. Am. Chem. Soc., 1980, 102 (19), pp
7 ne of the key steps + stereochemical explanation MsN 3 (1.3 equiv.) Et 3 N (3.0 equiv.) Rh 2 (Ac) 4 (5 mol%) (20.0 equiv.) CF 3 TBS MeCN, rt, 5 h 61% N 2 TBS toluene, 65 C, 1 h 60%, dr 3:1 TBS Rh-mediated - insertion + Claisen rearrangement Rh 2 (Ac) 4 - insertion to carbene N 2 TBS metal carbenoid formation Rh TBS TBS Major TS Minor TS TBS [3,3]-sigmatropic rearrangement (Claisen rearrangement) via C 3 C 3 C 3 TBS or 3 C C 3 C 3 TBS TBS 7
8 Synthesis completion enabled by biomimetic aldol MsN 3 (1.3 equiv.) Et 3 N (3.0 equiv.) Rh 2 (Ac) 4 (5 mol%) (20.0 equiv.) CF 3 TBS MeCN, rt, 5 h 61% N 2 TBS toluene, 65 C, 1 h 60%, dr 3:1 TBS Rh-mediated - insertion + Claisen rearrangement Ca(Me) 2 (2.0 equiv.) Me, rt, 44 h 70%, dr 3:1 dr 14:1 after separation TBS F (aq.; 11.2 equiv.) MeCN/TF 1:1, rt, 24 h DMP (2.0 equiv.) NaC 3 (8.0 equiv.) DCM, 0 C, 2 h 45 min 86% over 2 steps [1,2]-allyl shift 3, Sudan III (spatula tip) pyridine (4.0 equiv.) DCM/Me, -78 C <1 min then PPh 3 (2.0 equiv.) rt, 1 h 88% P Ph Ph (0.5 equiv.) toluene, 65 C, 100 min 71% dr 10:1 Biomimetic phosphonic-acid catalyzed aldol cyclization C 3 C3 LMDS (4.0 equiv.) PhSeCl (2.0 equiv.) TF, -78 C, 3.5 h then NaI 4 (aq.; 12 equiv.) -78 C to rt, 1.5 h 45% Ac Ac I Ac C TMS 3 N TMS Me S N N Li N 3 C3 N N Ph LMDS MsN 3 Periconianone A DMP Sudan III 8
9 Congrats to the Gademann group at U. of Zurich 9
10 Go Green! 10
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