Synthesis of the ABC fragment of calyciphylline A-type Daphniphyllum alkaloids

Tetrahedron

Volumn 71, Issue 22, 2015, Pages 3642-3651

  Diaba, Faïza ^a   Martínez Laporta, Agustín ^a   Coussanes, Guilhem ^a   Fernández, Israel ^b   Bonjoch, Josep ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

Alkaloids; Atom transfer radical cyclization; Cesium effect; Kinetic versus thermodynamic stereocontrol; Natural product synthesis; Sulfone based intramolecular Michael

Indexed keywords

ALKALOID; CALYCIPHYLLINE A DAPHNIPHYLLUM ALKALOID; CARBONIC ACID; CESIUM ION; KETONE DERIVATIVE; POTASSIUM ION; SULFONE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; CYCLOPROPANATION; DEBENZYLATION; DEHYDROGENATION; DENSITY FUNCTIONAL THEORY; EPIMER; HYDROGENATION; HYDROGENOLYSIS; HYDROLYSIS; MICHAEL ADDITION; MICROWAVE IRRADIATION; NUCLEOPHILICITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

DAPHNIPHYLLUM;

EID: 84929103329     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.11.044     Document Type: Article

References (65)

1. For a review, see: B. Kang, P. Jakubec, and D. Dixon J. Nat. Prod. Rep. 31 2014 550 562
2. D. Solé, X. Urbaneja, and J. Bonjoch Org. Lett. 7 2005 5461 5464
3. For our studies on 3-substituted cis-3a-methyloctahydroindole compounds (AC ring), see
4. A. Cordero-Vargas, X. Urbaneja, and J. Bonjoch Synlett 2007 2379 2382
5. A. Cordero-Vargas, B. Bradshaw, and J. Bonjoch Tetrahedron 64 2008 8134 8140
6. Z. Lu, Y. Li, J. Deng, and A. Li Nat. Chem. 5 2013 679 684
7. X. Xiong, Y. Li, Z. Lu, M. Wan, J. Deng, S. Wu, H. Shao, and A. Li Chem. Commun. 2014 5294 5297
8. Y. Yao, and G. Liang Org. Lett. 14 2012 5499 5501
9. A.A. Ibrahim, A.N. Golonka, A.M. Lopez, and J.L. Stockdill Org. Lett. 16 2014 1072 1075
10. For other synthetic studies leading to tri- and tetracyclic fragments of calyciphylline A-type alkaloids, see: ACD ring
11. C. Xu, Z. Liu, H. Wang, B. Zhang, Z. Xiang, X. Hao, and D.Z. Wang Org. Lett. 13 2011 1812 1815
12. F. Sladojevich, I.N. Michaelides, B. Darses, J.W. Ward, and D.J. Dixon Org. Lett. 13 2011 5132 5235
13. L. Wang, C. Xu, L. Chen, X. Hao, and D.Z. Wang Org. Lett. 16 2014 1076 1079 BCD ring
14. S. Ikeda, M. Shibuya, N. Kanoh, and Y. Iwabuchi Org. Lett. 11 2009 1833 1836 DEF ring
15. B. Darses, I.N. Michaelides, F. Sladojevich, J.W. Ward, P.R. Rzepa, and D.J. Dixon Org. Lett. 14 2012 1684 1687 ABCD ring
16. C. Xu, L. Wang, X. Hao, and D.Z. Wang J. Org. Chem. 77 2012 6307 6313
17. For Dixon's pioneering use of the intramolecular Michael reaction to build ring B in studies toward calychiphille A-type alkaloids, see Ref. 8b.
18. For a review on the synthesis of 2-azabicyclo[3.3.1]nonanes, see: J. Bonjoch, F. Diaba, and B. Bradshaw Synthesis 2011 993 1018
19. For a classical review, see: C.P. Jasperse, D.P. Curran, and T.L. Flevig Chem. Rev. 91 1991 1237 1286
20. J. Bonjoch, B. Bradshaw, and F. Diaba V. Andrushko, N. Andrushhko, Stereoselective Synthesis of Drugs and Natural Products 2013 Wiley-VCH New York, NY 733 768
21. J. Quirante, C. Escolano, A. Merino, and J. Bonjoch J. Org. Chem. 63 1998 968 976
22. J. Cassayre, B. Quiclet-Sire, J.-B. Saunier, and S.Z. Zard Tetrahedron Lett. 39 1998 8995 8998
23. J. Cassayre, and S.Z. Zard Synlett 1999 501 503
24. J.A. Seijas, M.P. Vázquez-Tato, L. Castedo, R.J. Estévez, M.G. Onega, and M. Ruiz Tetrahedron 48 1992 1637 1642
25. Q. Li, G. Li, S. Ma, P. Feng, and Y. Shi Org. Lett. 15 2013 2601 2603
26. F. Diaba, A. Martínez-Laporta, and J. Bonjoch J. Org. Chem. 79 2014 9365 9372
27. Throughout the discussion, the systematic numbering for each compound is used. Thus, the numbering depicted in Scheme 1 is only applicable to azatricyclic compounds and not to 2-azabicyclo[3.3.1]nonane derivatives (see compound 4 in Scheme 2).
28. J. Quirante, C. Escolano, M. Massot, and J. Bonjoch Tetrahedron 53 1997 1391 1402
29. F. Diaba, A. Martínez-Laporta, and J. Bonjoch Eur. J. Org. Chem. 2014 2371 2378
30. Radicals formed from the decomposition of the free radical initiator 2,2′-azobisisobutyronitrile (AIBN) at 60 °C continuously regenerate the catalytically active lower oxidation state transition metal complex (activator) by the abstraction of a halogen atom from the higher oxidation state complex (deactivator). See: W.T. Eckenhoff, and T. Pintauer Catal. Rev. Sci. Eng. 52 2010 1 59
31. F. Diaba, A. Martínez-Laporta, J. Bonjoch, A. Pereira, J.M. Muñoz-Molina, P.J. Pérez, and T.R. Belderrain Chem. Commun. 2012 8799 8801
32. For the synthesis of cyclopropanes from 1,3-dihalides, see
33. M.A. Fernández-Zúmel, C. Buron, and K. Severin Eur. J. Org. Chem. 2011 2272 2277
34. J. Risse, M.A. Fernández-Zúmel, Y. Cudré, and K. Severin Org. Lett. 14 2012 3060 3063
35. M.M. Cid, and E. Pombo-Villar Helv. Chim. Acta 76 1993 1591 1607
36. For a seminal study, see: B. Trost, and R.A. Kunz J. Org. Chem. 39 1974 2475 2476
37. The chemical shift of C-4 (δ 41.7) and C-9 (δ 24.5) of a sample of epi-8 (see Experimental part) is also in agreement with the stereochemical elucidation.
38. 13C NMR data for substituted 2-azabicyclo[3.3.1nonan-3-ones, see: J. Quirante, C. Escolano, F. Diaba, M. Torra, and J. Bonjoch Magn. Reson. Chem. 38 2000 891 893
39. 3) mainly returned the starting material.
40. For a review on 1,3-oxidative transpositions of allylic alcohols in organic synthesis, see: F.A. Luzzio Tetrahedron 68 2012 5323 5339
41. W.G. Dauben, and D.M. Michno J. Org. Chem. 42 1977 682 685
42. Treatment of 11 with hot water returned only the starting material. For this procedure promoting 1,3-rearrangement of allylic alcohols, as well as examples mediated by Bronsted acids, see: P.-F. Li, H.-L. Wang, and J. Qu J. Org. Chem. 79 2014 3955 3962
43. For related problems in the Dauben oxidation in structurally demanding allylic tertiary alcohols, see
44. E. Jiménez-Núñez, K. Molawi, and A.M. Echavarren Chem. Commun. 2009 7327 7329
45. K.K. Larson, and R. Sarpong J. Am. Chem. Soc. 131 2009 13244 13245
46. R.V.S. Nirogi, J.B. Konda, R. Kambhampati, A. Shinde, T.R. Bandyala, P. Gudla, K.K. Kandukuri, P. Jayarajan, V. Kandikere, and P.K. Dubey Bioorg. Med. Chem. Lett. 22 2012 6980 6985
47. 2 (5 mol %, toluene, 115 °C, 3 h, 55% yield, 68% based on recovered starting material).
48. T. Diao, and S.S. Stahl J. Am. Chem. Soc. 133 2011 14566 14569
49. C.M. Woo, S.L. Gholap, L. Lu, M. Kaneko, Z. Li, P.C. Ravikumar, and S.B. Herzon J. Am. Chem. Soc. 134 2012 17262 17273
50. 2; IBX, TsOH, DMSO) were unsuccessful.
51. R.C. Larock, T.R. Hightower, G.A. Kraus, P. Hahn, and D. Zheng Tetrahedron Lett. 36 1995 2423 2426 and references therein
52. 2, see: H. Fujishima, H. Takeshita, S. Suzuki, M. Toyota, and M. Ihara J. Chem. Soc., Perkin Trans. 1 1999 2609 2616
53. G. Dijkstra, W.H. Kruizinga, and R.M. Kellogg J. Org. Chem. 52 1987 4230 4234
54. It is believed that the cesium effect stems from:(i) better solubility of cesium bases and the generation of highly reactive 'naked' anions; (ii) the large size of Cs; and (iii) its facile polarizability: D.G. Musaev, T.M. Figg, and A.L. Kaledin Chem. Soc. Rev. 43 2014 5009 5031
55. For the importance of alkali metal counterions as stereocontrol elements in cyclization processes, see for example: Y. Hu, R.L. Bishop, A. Luxenburger, S. Dong, and L.A. Paquette Org. Lett. 8 2006 2735 2737
56. rel=24 (0.1), 25 (0.0) at B3LYP-D3/6-31+G(d) level.
57. 1H chemical shifts in the NMR of sulphones, see: R.J. Abraham, J.J. Byrne, and L. Griffiths Magn. Reson. Chem. 46 2008 667 675
58. J.E. Gurst, R.W. Miller, and A.T. McPhail Tetrahedron Lett. 21 1980 3223 3226
59. B. Kasum, and R.H. Prager Aust. J. Chem. 43 1990 63 68
60. Compound 2 was synthesized following our previously reported procedure (Ref. 16), using trichloroacetyl chloride as the acylating agent.
61. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, M.J. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, and D.J. Fox Gaussian 09, Revision D.01 2009 Gaussian Wallingford, CT
62. Y. Zhao, and D.G. Truhlar Theor. Chem. Acc. 120 2008 215 241
63. W.J. Hehre, L. Radom, P.v.R. Scheleyer, and J.A. Pople Ab Initio Molecular Orbital Theory 1986 Wiley New York, NY 66 88 and references therein
64. J.W. McIver, and A. Komornicki J. Am. Chem. Soc. 94 1972 2625 2633
65. C. González, and H.B. Schlegel J. Phys. Chem. 94 1990 5523 5527