Pure and Applied Chemistry

Pure Appl. Chem., 2012, Vol. 84, No. 7, pp. 1597-1619

http://dx.doi.org/10.1351/PAC-CON-11-10-12

Published online 2012-05-22

Stereoselective construction of 5,11‑methanomorphanthridine and 5,10b‑phenanthridine structural frameworks: Total syntheses of (±)-pancracine, (±)‑brunsvigine, (±)-maritidine, and (±)-crinine

References

• 1. O. Hoshino. In The Alkaloids, Vol. 1, G. A. Cordell (Ed.), p. 323, Academic Press, New York (1998).
• 2. S. F. Martin. In The Alkaloids, Vol. 30, A. Brossi (Ed.), p. 251, Academic Press, New York (1987).
• 3. W. C. Wildman. In The Alkaloids, Vol. 6, R. H. F. Manske (Ed.), p. 290, Academic Press, New York (1965).
• 4. J. R. Lewis. Nat. Prod. Rep. 10, 291 (1993). (http://dx.doi.org/10.1039/np9931000291)
• 5. N. Thi Ngoc Tram, Tz. V. Titorenkova, V. St. Bankova, N. V. Handjieva, S. S. Popov. Fitoterapia 73, 183 (2002). (http://dx.doi.org/10.1016/S0367-326X(02)00068-0)
• 6. C. W. Fennell, J. van Staden. J. Ethnopharmacol. 78, 15 (2001). (http://dx.doi.org/10.1016/S0378-8741(01)00305-1)
• 7a. G. Pandey, G. Lakshmaiah, G. Kumaraswamy. J. Chem. Soc., Chem. Commun. 1313 (1992). (http://dx.doi.org/10.1039/c39920001313)
• 7b. G. Pandey, G. Lakshmaiah. Tetrahedron Lett. 34, 4861 (1993). (http://dx.doi.org/10.1016/S0040-4039(00)74110-4)
• 8. G. Pandey, P. Banerjee, R. Kumar, V. G. Puranik. Org. Lett. 7, 3713 (2005). (http://dx.doi.org/10.1021/ol051321o)
• 9. G. Pandey, R. Kumar, P. Banerjee, V. Puranik. Eur. J. Org. Chem. 4571 (2011). (http://dx.doi.org/10.1002/ejoc.201100601)
• 10. G. Pandey, N. R. Gupta, T. M. Pimpalpalle. Org. Lett. 11, 2547 (2009). (http://dx.doi.org/10.1021/ol900806m)
• 11. G. Pandey, N. R. Gupta, S. R. Gadre. Eur. J. Org. Chem. 740 (2011). (http://dx.doi.org/10.1002/ejoc.201001263)
• 12a. M. Ishizaki, O. Hoshino, Y. Iitaka. Tetrahedron Lett. 32, 7079 (1991). (http://dx.doi.org/10.1016/0040-4039(91)85045-7)
• 12b. M. Ishizaki, O. Hoshino. J. Org. Chem. 57, 7285 (1992). (http://dx.doi.org/10.1021/jo00052a051)
• 13a. J. Jin, S. M. Weinreb. J. Am. Chem. Soc. 119, 2050 (1997). (http://dx.doi.org/10.1021/ja963900h)
• 13b. J. Jin, S. M. Weinreb. J. Am. Chem. Soc. 119, 5773 (1997). (http://dx.doi.org/10.1021/ja970839n)
• 14. M. Ishizaki, K.-I. Kurihara, E. Tanazawa, O. Hoshino. J. Chem. Soc., Perkin Trans. 1 101 (1993). (http://dx.doi.org/10.1039/p19930000101)
• 15a. L. E. Overman, J. Shim. J. Org. Chem. 56, 5005 (1991). (http://dx.doi.org/10.1021/jo00017a002)
• 15b. L. E. Overman, J. Shim. J. Org. Chem. 58, 4662 (1993). (http://dx.doi.org/10.1021/jo00069a032)
• 16. W. H. Pearson, B. W. Lian. Angew. Chem., Int. Ed. 37, 1724 (1998). (http://dx.doi.org/10.1002/(SICI)1521-3773(19980703)37:12<1724::AID-ANIE1724>3.0.CO;2-8)
• 17. M. Ikeda, M. Hamada, T. Yamashita, F. Ikegami, T. Sato, H. Ishibashi. Synlett 1246 (1998). (http://dx.doi.org/10.1055/s-1998-1937)
• 18a. C.-K. Sha, S.-J. Huang, C.-M. Huang, A.-W. Hong, T.-H. Jeng. Pure Appl. Chem. 72, 1773 (2000). (http://dx.doi.org/10.1351/pac200072091773)
• 18b. C.-K. Sha, A.-W. Hong, C.-M. Huang. Org. Lett. 3, 2177 (2001). (http://dx.doi.org/10.1021/ol016022n)
• 18c. A.-W. Hong, T.‑H. Cheng, V. Raghukumar, C.-K. Sha. J. Org. Chem. 73, 580 (2008).
• 19a. M. G. Banwell, A. J. Edwards, K. A. Jolliffe, M. Kemmler. J. Chem. Soc., Perkin Trans. 1 1345 (2001). (http://dx.doi.org/10.1039/b102252k)
• 19b. M. G. Banwell, O. J. Kokas, A. C. Willis. Org. Lett. 9, 3503 (2007). (http://dx.doi.org/10.1021/ol071344y)
• 19c. M. Matveenko, M. G. Banwell, A. C. Willis. Org. Lett. 10, 4693 (2008). (http://dx.doi.org/10.1021/ol801815k)
• 19d. O. J. Kokas, M. G. Banwell, A. C. Willis. Tetrahedron 64, 6444 (2008). (http://dx.doi.org/10.1016/j.tet.2008.04.070)
• 20. M.-Y. Chang, H.-P. Chen, C.-Y. Lin, C.-L. Pai. Heterocycles 65, 1999 (2005). (http://dx.doi.org/10.3987/COM-05-10470)
• 21. M. Anada, M. Tanaka, N. Shimada, H. Nambu, M. Yamawaki, S. Hashimoto. Tetrahedron 65, 3069 (2009). (http://dx.doi.org/10.1016/j.tet.2008.10.091)
• 22. S. V. Pansare, R. Lingampally, R. L. Kirby. Org. Lett. 12, 556 (2010). (http://dx.doi.org/10.1021/ol902761a)
• 23. The absence of NOESY cross-peaks for 4a-H–12-H and 11a-H–12-H clearly confirm the endo orientation of C-12 in 11 and J(C-11a,C-4a) = 8.74 Hz for the cis configuration of C-11a and C‑4a.
• 24. X-ray analysis of 30 (C₁₆H₁₉NO₄): CCDC-271169 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via <www.ccdc.cam.ac.uk/data_request/cif>.
• 25a. H. O. House, W. V. Phillips, T. S. V. Sayer, C. C. Yau. J. Org. Chem. 43, 700 (1978). (http://dx.doi.org/10.1021/jo00398a041)
• 25b. G. Petrovic, Z. Cekovic. Org. Lett. 2, 3769 (2000). (http://dx.doi.org/10.1021/ol0062401)
• 26. M. H. Howard, F. J. Sardina, H. Rapoport. J. Org. Chem. 55, 2829 (1990). (http://dx.doi.org/10.1021/jo00296a050)
• 27. W. J. Scott, J. K. Stille. J. Am. Chem. Soc. 108, 3033 (1986). (http://dx.doi.org/10.1021/ja00271a037)
• 28. D. L. Comins, A. Dehghani. Tetrahedron Lett. 33, 6299 (1992). (http://dx.doi.org/10.1016/S0040-4039(00)60957-7)
• 29a. T. Mukaiyama, M. Hayashi. Chem. Lett. 15 (1974). (http://dx.doi.org/10.1246/cl.1974.15)
• 29b. for the intramolecular version, see: T. Mukaiama. Org. React. 28, 238 (1982).
• 29c. T. Mukaiyama, M. Murakami. Synthesis 1043 (1987). (http://dx.doi.org/10.1055/s-1987-28167)
• 30a. Y. Yokozawa, T. Nakai, N. Ishikawa. Tetrahedron Lett. 25, 3987 (1984). (http://dx.doi.org/10.1016/0040-4039(84)80047-7)
• 30b. S. Murata, M. Suzuki, R. Noyori. Tetrahedron 44, 4259 (1988). (http://dx.doi.org/10.1016/S0040-4020(01)86671-0)
• 31. For recent reviews on aldol reactions, see.
• 31a. B. Alcaide, P. Amendros. Eur. J. Org. Chem. 1595 (2002) and refs. cited therein. (http://dx.doi.org/10.1002/1099-0690(200205)2002:10<1595::AID-EJOC1595>3.0.CO;2-M)
• 31b. C. Palomo, M. Oiarbide, J. M. Garcia. Chem.—Eur. J. 8, 36 (2002). (http://dx.doi.org/10.1002/1521-3765(20020104)8:1<36::AID-CHEM36>3.0.CO;2-L)
• 32. C. Johnstone, J. W. Kerr, J. S. Scott. Chem. Commun. 341 (1996). (http://dx.doi.org/10.1039/cc9960000341)
• 33. K. Tanemura, T. Suzuki, T. Horaguchi. J. Chem. Soc., Chem. Commun. 2997 (1992).
• 34. M. E. Jung, W. A. Andrus, P. L. Ornstein. Tetrahedron Lett. 18, 4175 (1977). (http://dx.doi.org/10.1016/S0040-4039(01)83458-4)
• 35. X-ray analysis of 41 (C₁₈H₂₁NO₅): CCDC-817475 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via <www.ccdc.cam.ac.uk/data_request/cif>.
• 36. For reviews of the HWE reaction, see.
• 36a. J. Boutagy, R. Thomas. Chem. Rev. 74, 87 (1974). (http://dx.doi.org/10.1021/cr60287a005)
• 36b. B. E. Maryanoff, A. B. Reitz. Chem. Rev. 89, 863 (1989). (http://dx.doi.org/10.1021/cr00094a007)
• 36c. S. E. Kelly. Comp. Org. Syn. 1, 729 (1991). (http://dx.doi.org/10.1016/B978-0-08-052349-1.00020-2)
• 37. K. Prantz, J. Mulzer. Chem. Rev. 110, 3741 (2010) and refs. cited therein. (http://dx.doi.org/10.1021/cr900386h)
• 38a. R. H. Grubbs. Handbook of Metathesis, Wiley-VCH, Weinheim (2003).
• 38b. R. H. Grubbs, T. M. Trnka. “Ruthenium-catalysed olefin metathesis”, in Ruthenium in Organic Chemistry, S.-I. Murahasi (Ed.), Wiley-VCH, Weinheim (2004).
• 39a. S. Elango, T.-H. Yan. J. Org. Chem. 67, 6954 (2002). (http://dx.doi.org/10.1021/jo020155k)
• 39b. S. Elango, T.-H. Yan. Tetrahedron 58, 7335 (2002). (http://dx.doi.org/10.1016/S0040-4020(02)00736-6)
• 40. G. C. Fu, S. T. Nguyen, R. H. Grubbs. J. Am. Chem. Soc. 115, 9856 (1993). (http://dx.doi.org/10.1021/ja00074a085)
• 41. D. L. Wright, J. P. Schulte II, M. A. Page. Org. Lett. 2, 1847 (2000). (http://dx.doi.org/10.1021/ol005903b)
• 42. Q. Yang, W.-J. Xiao, Z. Yu. Org. Lett. 7, 871 (2005). (http://dx.doi.org/10.1021/ol047356q)
• 43. K. Shimizu, M. Takimoto, Y. Sato, M. Mori. J. Organomet. Chem. 691, 5466 (2006). (http://dx.doi.org/10.1016/j.jorganchem.2006.08.013)
• 44a. K. V. Gothelf, K. A. Jørgensen. Chem. Rev. 98, 863 (1998). (http://dx.doi.org/10.1021/cr970324e)
• 44b. S. Karlsson, H.-E. Högsberg. Org. Prep. Proced. Int. 33, 103 (2001). (http://dx.doi.org/10.1080/00304940109356583)
• 44c. G. Pandey, P. Banerjee, S. R. Gadre. Chem. Rev. 106, 4484 (2006) and refs. cited therein. (http://dx.doi.org/10.1021/cr050011g)
• 45. I. Coldham, R. Hufton. Chem. Rev. 105, 2765 (2005) and refs. cited therein. (http://dx.doi.org/10.1021/cr040004c)
• 46. A. I. Meyers, M. J. McKennon. J. Org. Chem. 58, 3568 (1993).
• 47. HPLC conditions: Chiralcel column: OD-H (250_4.6 mm), ethanol/petroleum ether (10:90), flow rate 0.5 mL/min (280 psi), retention times of 27 and 30 min, ee (obsd.) ≈ 63 %.
• 48a. M. A. Schwartz, R. A. Holton. J. Am. Chem. Soc. 92, 1090 (1970). (http://dx.doi.org/10.1021/ja00707a074)
• 48b. M. A. Schwartz, B. F. Rose, R. A. Holton, S. W. Scott, B. Vishnuvajjala. J. Am. Chem. Soc. 99, 2571 (1977). (http://dx.doi.org/10.1021/ja00450a027)
• 49. Y. Kita, T. Takada, M. Gyoten, H. Tohma, M. H. Zenk, J. Eichhorn. J. Org. Chem. 61, 5857 (1996). (http://dx.doi.org/10.1021/jo9606766)
• 50a. T. Kametani, T. Kohno, S. Shibuya, K. Fukumoto. Tetrahedron 27, 5441 (1971). (http://dx.doi.org/10.1016/S0040-4020(01)91709-0)
• 50b. T. Kametani, T. Kohno, S. Shibuya, K. Fukumoto. J. Chem. Soc., Chem. Commun. 14, 774 (1971).
• 51a. S. Tobinaga, E. Kotani. J. Am. Chem. Soc. 94, 309 (1972). (http://dx.doi.org/10.1021/ja00756a071)
• 51b. E. Kotani, N. Takeuchi, S. Tobinaga. J. Chem. Soc., Chem. Commun. 550 (1973). (http://dx.doi.org/10.1039/c39730000550)
• 51c. E. Kotani, N. Takeuchi, S. Tobinaga. Tetrahedron Lett. 14, 2735 (1973). (http://dx.doi.org/10.1016/S0040-4039(01)96125-8)
• 52a. S. Yamada, K. Tomioka, K. Koga. Tetrahedron Lett. 17, 57 (1976). (http://dx.doi.org/10.1016/S0040-4039(00)71322-0)
• 52b. S. Yamada, K. Tomioka, K. Koga. Tetrahedron Lett. 17, 61 (1976). (http://dx.doi.org/10.1016/S0040-4039(00)71323-2)
• 52c. K. Tomioka, K. Koga, S. Yamada. Chem. Pharm. Bull. 25, 2681 (1977). (http://dx.doi.org/10.1248/cpb.25.2681)
• 52d. K. Tomioka, K. Shimizu, S. Yamada, K. Koga. Heterocycles 6, 1752 (1977).
• 53. G. Ma, H. Y. Li, C. Lu, X. Yang, S. Hong. Heterocycles 24, 2089 (1986). (http://dx.doi.org/10.3987/R-1986-08-2089)
• 54. S. Ghosal, S. Singh, R. S. Srivastava. Phytochemistry 25, 1975 (1986). (http://dx.doi.org/10.1016/S0031-9422(00)81187-5)
• 55. M. Kihara, T. Koike, Y. Imakura, K. Kia, T. Shingu, S. Kobayashi. Chem. Pharm. Bull. 35, 1070 (1987). (http://dx.doi.org/10.1248/cpb.35.1070)
• 56. J. Bastida, J. M. Llabres, F. Viladomat, C. Codina, M. Rubiralta, M. Feliz. Planta Med. 54, 524 (1988). (http://dx.doi.org/10.1055/s-2006-962537)
• 57. M. R. Herrera, R. Brun, F. Villadoma, C. Codina, J. Bastida. Planta Med. 67, 191 (2001). (http://dx.doi.org/10.1055/s-2001-11495)
• 58. H. Muxfeldt, R. S. Schneider, J. B. Mooberry. J. Am. Chem. Soc. 88, 3670 (1966). (http://dx.doi.org/10.1021/ja00967a052)
• 59. J. B. P. A. Wijnberg, W. N. Speckamp. Tetrahedron 34, 2579 (1978). (http://dx.doi.org/10.1016/0040-4020(78)88390-2)
• 60. G. E. Keck, R. R. Webb. J. Org. Chem. 47, 1302 (1982). (http://dx.doi.org/10.1021/jo00346a028)
• 61. J. P. Michael, A. S. Howard, R. B. Katz, M. I. Zwane. Tetrahedron Lett. 33, 6023 (1992). (http://dx.doi.org/10.1016/S0040-4039(00)61117-6)
• 62. H. W. G. L. Smith Jr. J. Am. Chem. Soc. 89, 3600 (1967).
• 63a. L. E. Overman, L. T. Mendelson. J. Am. Chem. Soc. 103, 5579 (1981). (http://dx.doi.org/10.1021/ja00408a055)
• 63b. L. E. Overman, L. T. Mendelson, E. J. Jacobson. J. Am. Chem. Soc. 105, 6629 (1983). (http://dx.doi.org/10.1021/ja00360a014)
• 63c. L. E. Overman, S. Sugai. Helv. Chim. Acta 68, 745 (1985). (http://dx.doi.org/10.1002/hlca.19850680324)
• 64a. S. F. Martin, C. L. Campbell. Tetrahedron Lett. 28, 503 (1987). (http://dx.doi.org/10.1016/S0040-4039(00)95766-6)
• 64b. S. F. Martin, C. L. Campbell. J. Org. Chem. 53, 3184 (1988). (http://dx.doi.org/10.1021/jo00249a011)
• 65. W. H. Pearson, H. E. Lovering. Tetrahedron Lett. 35, 9173 (1994). (http://dx.doi.org/10.1016/0040-4039(94)88457-9)
• 66a. N. T. Tam, J. Chang, E.-J. Jung, C.-G. Cho. J. Org. Chem. 73, 6258 (2008). (http://dx.doi.org/10.1021/jo8008353)
• 66b. N. T. Tam, C.‑G. Cho. Org. Lett. 10, 601 (2008). (http://dx.doi.org/10.1021/ol702907u)
• 67a. M. Bohno, H. Imase, N. Chida. Chem. Commun. 1086 (2004). (http://dx.doi.org/10.1039/b402762k)
• 67b. M. Bohno, K. Sugie, H. Imase, Y. B. Yusof, T. Oishi, N. Chida. Tetrahedron 63, 6977 (2007). (http://dx.doi.org/10.1016/j.tet.2007.05.041)
• 68a. C. Bru, C. Thal, C. Guillou. Org. Lett. 5, 1845 (2003). (http://dx.doi.org/10.1021/ol0343358)
• 68b. C. Bru, C. Thal, C. Guillou. Tetrahedron 62, 9043 (2006). (http://dx.doi.org/10.1016/j.tet.2006.07.005)
• 69. I. H. Sanchez, F. J. Lopez, J. J. Soria, M. I. Larraza, H. J. Flores. J. Am. Chem. Soc. 105, 7640 (1983). (http://dx.doi.org/10.1021/ja00364a029)
• 70. X. Han, B. M. Stoltz, E. J. Corey. J. Am. Chem. Soc. 121, 7600 (1999). (http://dx.doi.org/10.1021/ja991500z)
• 71. H. X. Zhang, F. Guibe, G. Balavoine. J. Org. Chem. 55, 1857 (1990). (http://dx.doi.org/10.1021/jo00293a035)
• 72. C. V. Wilson, D. E. Janssen. Organic Synthesis, collective Vol. IV, p. 547, John Wiley, New York (1963).
• 73. P. Beak, E. K. Yum. J. Org. Chem. 58, 823 (1993). (http://dx.doi.org/10.1021/jo00056a010)
• 74. X. Han, B. M. Stoltz, E. J. Corey. J. Am. Chem. Soc. 121, 7600 (1999). (http://dx.doi.org/10.1021/ja991500z)
• 75. J. L. Luche, L. Rodriguez-Hahn, P. Crabbe. J. Chem. Soc., Chem. Commun. 601 (1978). (http://dx.doi.org/10.1039/c39780000601)
• 76. J. McNulty, J. J. Nair, C. Codina, J. Bastida, S. Pandey, J. Gerasimoff, C. Griffin. Phytochemistry 68, 1068 (2007). (http://dx.doi.org/10.1016/j.phytochem.2007.01.006)