Synthesis of the Stenine Ring System from Pyrrole
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1 Current Literature Presentation gor psenica 06/18/2011 Synthesis of the Stenine Ring System from Pyrrole Bates, R. W.; Sridhar, S. J. rg. Chem., 2011, 76, gor Wipf Group Page 1 of 16 6/18/2011
![The Stemonaceae family is still the only source of the Stemona alkaloids The Stemona alkaloids are: structurally characterized by the presence pyrrolo[1,2-a]azepine core pyrido[1,2-a]azepine core](/docs-images/92/109437333/images/2-0.jpg "currently comprises 139 alkaloids Stenine Stemona sessilifolia The Stemona alkaloids can be organize into eight groups: stenine (), stemoamide (), tuberostemospironine (), stemonamine (V),")
2 The Stemonaceae family is still the only source of the Stemona alkaloids The Stemona alkaloids are: structurally characterized by the presence pyrrolo[1,2-a]azepine core pyrido[1,2-a]azepine core currently comprises 139 alkaloids Stenine Stemona sessilifolia The Stemona alkaloids can be organize into eight groups: stenine (), stemoamide (), tuberostemospironine (), stemonamine (V), parvistemoline (V), stemofoline (V) (all of which contain the pyrrolo[1,2-a]azepine core) V 8 9 9a A V R stemocurtisine (V) displaying the pyrido[1,2-a]azepine nucleus, miscellaneous group V at. Prod. Rep., 2010, 27, 1908 V gor Wipf Group Page 2 of 16 6/18/2011
3 Chen, C.; art, D. J. J. rg. Chem., 1990, 55, 6236 C2 Me Me 2 C2 Me C2 Me C2 Me ( )-Stenine EtAlCl 3 CCl 3, 85 C intramolecular Diels-Alder reaction Ac Me 3 1. Mesytilene, Δ 2. Me Curtius rearrangement Ac C 2 Me ring D: Claisen Eschenmoser rearrangement and iodolactonization ring B: intramolecular lactam formation C2 Me MeLi, TF Ms C 2 Me D Ac C B A gor Wipf Group Page 3 of 16 6/18/2011
4 Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1995, 117, Wipf, P.; Spencer, S. R. J. Am. Chem. Soc. 2005, 127, 225 Cbz Me 2 C2 Bn C2 Bn C 2 Me C 2 Bn C 2 (-)-Stenine TPS TPS C 2 Bn C 2 -benzyloxycarbonyltyrosine Ph(Ac) 2, ac 3 Me, C C 2 Me C2 Bn D C B A Me 2 C 2 Me C2 Bn 3 CC(Me) 2 Me C C 2 Me C2 Bn ring D: Claisen Eschenmoser rearrangement and iodolactonization ring B: intramolecular lactam formation PhSe C 2 Me Cbz C 2 Tuberostemonin Ph gor Wipf Group Page 4 of 16 6/18/2011
5 Morimoto, Y.; wahashi, M.; ishida, K.; ayashi, Y.; Shirahama,. Angew. Chem. nt. Ed. Engl., 1996, 35, 904 (-)-Stenine MPM C2 Me MPM C 2 Me MPM S S Ph (Et) 2 P Ph S S MPM TP Cl TMS MPM C 2 Me 1. MCPBA, hexane, DCM, -15 C-rt , TF, 2, rt 2, ac 3, rt MPM C2 Me D C B A ring B: intramolecular nitrogen alkylation gor Wipf Group Page 5 of 16 6/18/2011
6 Frankowski, K. J.; Golden, J. E.; Zeng, Y.; Lei, Y.; Aube, J. J. Am. Chem. Soc. 2008, 130, 6018 Bn Bn 3 Bn 3 Bn TBS ( )-Stenine TMS 3 TMS 3 Bn 3 MeAlCl 2 C 2 Cl 2, 45 C Bn R Tandem Diels-Alder/Schmidt reaction Bn 2 R D C B A ring D: iodolactonization gor Wipf Group Page 6 of 16 6/18/2011
7 ( )-eostenine C 2 2 C Cl Cl Lainchbury, M. D.; Medley, M..; Taylor, P. M.; irst, P.; Dohle, W.; Booker-Milburn, K.. J. rg. Chem., 2008, 73, 6497 C 2 2 C + C 2 2 C ring C / D: ring A / B: hν [5+2] A B C D gor Wipf Group Page 7 of 16 6/18/2011
8 Padwa, A.; Ginn. J. D. J. rg. Chem. 2005, 70, 5197 MeS C 2 Me MeS MeS C 2 Me Et ( )-Stenine C 2 Me S S BF 4 C 2 Me C 2 Me MeS DMTSF MeS Et 3 MeS Et Et Et MeS intramolecular [4+2] cycloaddition rearrangement cascade reaction MeS C 2 Me MeS C 2 Me SMe C 2 Me D C B A gor Wipf Group Page 8 of 16 6/18/2011
9 Bates, R. W.; Sridhar, S. J. rg. Chem., 2011, 76, The Stemona alkaloids are attractive synthetic targets due to the diversity of structures found in this family of alkaloids Recently, it has been reported that neostenine, a stereoisomer of stenine, has antitussive activity comparable to that of codeine Using pyrroles in natural product synthesis is challenging: highly electron-rich nature of the pyrrole ring promote certain productive reactions, but it can also cause some problems Additional synthetic strategies has been used to construct the pyrrole moiety in pyrrole-containing natural products R C gor Wipf Group Page 9 of 16 6/18/2011
10 R C Ms a, DMS, rt 87% C Grubbs, DCM, Δ 86% C McMillan's catalyst Bn TF, -20 o C ab 4, Et, rt 75%, 95% ee (two steps) C gor Wipf Group Page 10 of 16 6/18/2011
11 i) F 3 C ii) TBS i) 1) ( C) 2, Et 2, rt, 83%; 2) Cl, DCM, rt, 88% ii) 1) PVP, Me, rt, quant.; 2) TBSCl, imidazole, DCM, rt, quant. i) Cl 3 C CCl 3 ii) TBS Me i) 1) CCl 3 CCl, Et 2, rt, 95%; 2) Cl, DCM, rt, 90% ii) 1) ame, Me, rt, 90%.; 2) TBSCl, imidazole, DCM, rt, 80% gor Wipf Group Page 11 of 16 6/18/2011
12 R C CBr 4, PPh 3, CaC 3 : 60% CBr 4, PPh 3, Et 3 : no reaction Br TBS Pd/C, Cu, K 2 C 3 CBr 4, PPh 3 Ph TBS 3 P, DME, 85 C TBS CF collidine, DCM, 0 C 3 87% 83% Ambrelyst-15, Me, 14h, rt: 0% PPTS, Me, 10h, rt: 0% TBAF, TF, 14h, rt: 48% corresponding fluoride Ambrelyst-15 i-pr, 24h, rt 90% Br Br n, Ac, DMF, -40 C 52% DMP, DCM, rt 84% no diastereoselectivity using zinc (Zn) slight improvement with stannous chloride (SnCl 2 ) gor Wipf Group Page 12 of 16 6/18/2011
13 R C Ru 3 (C) 12, dioxane, Et 3 C, 100 C, 100 psi a, CF 2, DMS, rt 3 87% 99% gor Wipf Group Page 13 of 16 6/18/2011
14 a, 2, DMS, rt 90% Ru 3 (C) 12, dioxane, collidine C, 100 C, 100 psi 68% 14% Cyclocarbonylation of Allenol - Ru 3 (C) 12, C catalyst yield of yield of reagent loading / butenolid enone and solvent mol% (%) (%) dioxane, Et 3 (6 eq) a Et 3 (neat) b 2,4,6-collidine (neat) c dioxane, collidine (6 eq) c a A ca. 2:1 mixture of E/Z isomers. b A ca. 10:1 mixture. c ne isomer. Possible Mechanism of Ruthenium-Catalyzed Cyclocarbonylation J. rg. Chem. 2003, 68, gor Wipf Group Page 14 of 16 6/18/2011
15 R C a, 2, DMS, rt 90% Ru 3 (C) 12, dioxane, collidine C, 100 C, 100 psi 68% 14% C 2 DCM / 40 o C 90% 2 Mg, Me, rt 45% <5% 22% gor Wipf Group Page 15 of 16 6/18/2011
16 CCLUS Additional contribution to the synthesis of the stemona alkaloids using an new synthetic approach The high electron density of the pyrrole ring can complicate some reactions but can be controlled by using the trifluoroacetyl group, that can easily and rapidly be removed C McMillan's catalyst ring B C Br ring C ntramolecular Propargylic Barbier Reaction Ru-Catalyzed Cyclocarbonylation ring D gor Wipf Group Page 16 of 16 6/18/2011
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