Experimental and computational studies into an ATPH-Promoted exo-selective IMDA reaction: A short total synthesis of Δ 9-THC

Chemistry - A European Journal

Volumn 16, Issue 28, 2010, Pages 8280-8284

  Pearson, Emma L ^a   Kanizaj, Nicholas ^a   Willis, Anthony C ^a   Paddon Row, Michael N ^b   Sherburn, Michael S ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^b UNIVERSITY OF NEW SOUTH WALES   (Australia)

Author keywords

Cannabinoids; Density functional calculations; Diastereoselectivity; Diels alder reactions; Total synthesis

Indexed keywords

CANNABINOIDS; DENSITY-FUNCTIONAL CALCULATIONS; DIASTEREO-SELECTIVITY; DIELS-ALDER REACTION; TOTAL SYNTHESIS;

STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

CYCLOADDITION;

ALUMINUM TRIS(2,6 DIPHENYLPHENOXIDE); ALUMINUM TRIS(2,6-DIPHENYLPHENOXIDE); CANNABINOID; CYCLOALKANE DERIVATIVE; ORGANOMETALLIC COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

CANNABINOIDS; CYCLIZATION; CYCLOPARAFFINS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 77954837403     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201001176     Document Type: Article

References (48)

1. Y. Gaoni, R. Mechoulam, J. Am. Chem. Soc. 1964, 86, 1646-1647.
2. G. A. Thakur, R. I. Duclos, Jr., A. Makriyannis, Life Sci. 2005, 78, 454-466.
3. Representative examples: a) R. Mechoulam, Y. Gaoni, J. Am. Chem. Soc. 1965, 87, 3273-3275;
4. b) K. E. Fahrenholtz, M. Lurie, R. W. Kierstead, J. Am. Chem. Soc. 1967, 89, 5934-5941;
5. c) R. K. Razdan, H. C. Dalzell, G. R. Handrick, J. Am. Chem. Soc. 1974, 96, 5860-5865;
6. d) G. R. Handrick, R. K. Razdan, D. B. Uliss, H. C. Dalzell, E. Boger, J. Org. Chem. 1977, 42, 2563-2568;
7. e) W. E. Childers, Jr., H. W. Pinnick, J. Org. Chem. 1984, 49, 5276-5277;
8. f) M. Moore, R. W. Rickards, H. Rønneberg, Aust. J. Chem. 1984, 37, 2339-2348;
9. g) R. W. Rickards, H. Rønneberg, J. Org. Chem. 1984, 49, 572-573;
10. h) L. Crombie, W. M. L. Crombie, S. V. Jamieson, C. J. Palmer, J. Chem. Soc. Perkin Trans. 1 1988, 1243-1250;
11. i) A. D. William, Y. Kobayashi, Org. Lett. 2001, 3, 2017-2020;
12. j) A. D. William, Y. Kobayashi, J. Org. Chem. 2002, 67, 8771-8782;
13. k) B. M. Trost, K. Dogra, Org. Lett. 2007, 9, 861-863.
14. For reviews of syntheses of cannabinoids, see: a) R. K. Razdan in The Total Synthesis of Natural Products, Vol. 4 (Ed.: J. ApSimon), Wiley, New York, 1981, pp. 185-262;
15. b) R. Mechoulam, N. K. McCallum, S. Burstein, Chem. Rev. 1976, 76, 75-112.
16. a) M. A. Tius, A. Makriyannis, X. L. Zou, V. Abadji, Tetrahedron 1994, 50, 2671 -2680;
17. b) D. J. Drake, R. S. Jensen, J. Busch-Petersen, J. K. Kawakami, M. C. Fernandez-Garcia, P. Fan, A. Makriyannis, M. A. Tius, J. Med. Chem. 1998, 41, 3596-3608;
18. c) P. E. Harrington, I. A. Stergiades, J. Erickson, A. Makriyannis, M. A. Tius, J. Org. Chem. 2000, 65, 6576-6582;
19. d) A. Mahadevan, C. Siegel, B. R. Martin, M. E. Abood, I. Beletskaya, R. K. Razdan, J. Med. Chem. 2000, 43, 3778-3785.
20. Reviews: a) D. F. Taber, Intramolecular Diels-Alder and Alder Ene Reactions, Springer, Berlin, 1984;
21. b) A. G. Fallis, Can. J. Chem. 1984, 62, 183-234;
22. c) E. Ciganek, Org. React. 1984, 32, 1-374;
23. d) D. Craig, Chem. Soc. Rev. 1987, 16, 187-238;
24. e) W. R. Roush in Advances in Cycloaddition, Vol. 2 (Ed.: D. P. Curran), JAI, Greenwich, 1990, pp. 91.-146;
25. f) W. R. Roush in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon, Oxford, 1991, pp. 513-550;
26. g) T. Oh, M. Reilly, Org. Prep. Proced. Int. 1994, 26, 129-158;
27. th ed. (Eds.: G. Helmchen, R.W. Hoffmann, J. Mulzer, E. Schumann), Thieme, Stuttgart, 1995, pp. 2872-2904;
28. i) A. G. Fallis, Acc. Chem. Res 1999, 32, 464-474;
29. j) B. R. Bear, S. M. Sparks, K. J. Shea, Angew. Chem. 2001, 113, 864-894;
30. Angew. Chem. Int. Ed. 2001, 40, 820-849;
31. k) E. Marsault, A. Toró, P. Nowak, P. Deslongchamps, Tetrahedron 2001, 57, 4243-4260;
32. K.-i. Takao, R. Munakata, K.-i. Tadano, Chem. Rev. 2005, 105, 4779-4807.
33. a) K. Maruoka, H. Imoto, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 12115-12116;
34. b) S. Saito in Main Group Metals in Organic Synthesis, Vol.1 (Eds.: H. Yamamoto, K. Oshima), Wiley-VCH, Weinheim, 2004, pp. 189-306.
35. F. Korte, E. Dlugosch, U. Claussen, Liebigs Ann. Chem. 1966, 693, 165-170.
36. a) D. A. Evans, E. A. Shaughnessy, D. M. Barnes, Tetrahedron Lett. 1997, 38, 3193-3194;
37. b) D. A. Evans, D. M. Barnes, J. S. Johnson, T. Lectka, P. von Matt, S. J. Miller, J. A. Murry, R. D. Norcross, E. A. Shaughnessy, K. R. Campos, J. Am. Chem. Soc. 1999, 121, 7582-7594.
38. S. Inoue, C. Kosugi, Z. G. Lu, K. Sato, Nippon Kagaku Kaishi 1992, 45-52.
39. See the Supporting Information for full details.
40. T. Minami, Y. Matsumoto, S. Nakamura, S. Koyanagi, M. Yamaguchi, J. Org. Chem. 1992, 57, 167-173.
41. The relative configuration of IMDA adduct 2 was elucidated by single crystal X-ray analysis of cis-2c obtained from the deprotection of 2 a. See the Supporting Information for details. CCDC-772674 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.
42. AU calculations were carried out by using the Gaussian 03 program: Gaussian 03, Revision D.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 2003.
43. E. L. Pearson, L. C. H. Kwan, C. I. Turner, G. A. Jones, A. C. Willis, M.N. Paddon-Row, M.S. Sherburn, J. Org. Chem. 2006, 71, 6099-6109.
44. E. L. Pearson, A. C. Willis, M. S. Sherburn, M. N. Paddon-Row, Org. Biomol. Chem. 2008, 6, 513-522.
45. E. J. Corey, T. W. Lee, Chem. Commun. 2001, 1321-1329.
46. P. Yates, P. Eaton, J. Am. Chem. Soc. 1960, 82, 4436-4437.
47. S. Tsuzuki, K. Honda, T. Uchimaru, M. Mikami, K. Tanabe, J. Am. Chem. Soc. 2000, 122, 3746-3753.
48. Regulatory issues precluded the synthesis of the natural product.