Total synthesis of (-)-δ8- trans -Tetrahydrocannabinol

Synthesis

Volumn , Issue 11, 2010, Pages 1766-1770

  Huang, Qinggang ^a   Ma, Bin ^a   Li, Xian ^a   Pan, Xinfu ^a   She, Xuegong ^a,b  

^a LANZHOU UNIVERSITY   (China)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

Addition reactions; Deoxygenation; Heterocycles; Stereoselective synthesis; Tetrahydrocannabinol

Indexed keywords

DEOXYGENATIONS; ENOL SILYL ETHERS; HETEROCYCLES; STEREOSELECTIVE SYNTHESIS; TOTAL SYNTHESIS;

ADDITION REACTIONS; ETHERS; SYNTHESIS (CHEMICAL);

STEREOSELECTIVITY;

2 [6 ISOPROPENYL 3 METHYLCYCLOHEX 3 EN 1 YL] 1,3 BIS(METHOXYMETHOXY) 5 PENTYLBENZENE; 2 BROMO 1,3 BIS(METHOXYMETHOXY) 5 PENTYBENZENE; 4 BROMO 3,5 BIS(METHOXYMETHOXY)BENZYL METHANESULFONATE; 6 [ 2,6 BIS(METHOXYMETHOXY) 4 PENTYLPHENYL] 5 ISOPROPENYL 2 METHYLCYCLOHEX 2 EN 1 ONE; DELTA8 TETRAHYDROCANNABINOL; ENOL SILYL ETHER EPOXIDE; O [ 1 HYDROXY 6,6,9 TRIMETHYL 3 PENTYL 6A,7,10,10A TETRAHYDRO 6H BENZO[C]CHROMEN 10 YL] S METHYL DITHIOCARBONATE; O [6 [ 2,6 BIS(METHOXYMETHOXY) 4 PENTYLPHENYL] 5 ISOPROPENYL 2 METHYLCYCLOHEX 2 EN 1 YL] S METHYL DITHIOCARBONATE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANTIEMETIC ACTIVITY; ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION; DRUG DETERMINATION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROLYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 77952770467     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218732     Document Type: Article

References (55)

1. Taylor E C., Lenard K, Shvo Y, J. Am. Chem. Soc. 1966 88 367
2. Fahrenholtz K E., Lurie M, Kierstead R W., J. Am. Chem. Soc. 1967 89 5934
3. Binder M, Franke I, Schmidt B, Dietrich W, Helv. Chim. Acta 1982 65 807
4. Gernard C M., Mollereau C, Vassart G, Parmentier M, Biochem. J. 1991 279 129
5. Skaper S D., Buriani A, DalToso R, Petrelli L, Romamello S, Faca L, Leon A, Proc. Natl. Acad. Sci. U.S.A. 1996 93 3984
6. Matsuda L A., Lolait S J., Brownstein M J., Young A C., Bonner T I., Nature (London, U.K.) 1990 346 61
7. Munro S, Thomas K L., Abu-shaar M, Nature (London, U.K.) 1993 365 61
8. DiMarzo V, Goparaju S K., Wang L, Liu J, Batkai S, Jarai Z, Fezza F, Miura G I., Palmiter R D., Sugiuram T, Kunos G, Nature (London, U.K.) 2001 410 822
9. Parolaro D, Massi P, Rubino T, Monti E, Prostaglandins, Leukotrienes Essent. Fatty Acids 2002 66 319
10. Palmer S L., Thakur G A., Makriyannis A, Chem. Phys. Lipids 2002 121 3
11. Porcella A, Maxia C, Gessa G L., Pani L, Eur. J. Neurosci. 2001 13 409
12. Chien F Y., Wang R F., Mittag T W., Podos S M., Arch. Ophthalmol. 2003 121 87
13. For selected examples, see:, Mechoulam R, Gaoni Y, [nl]J. Am. Chem. Soc. 1965 87 3273
14. Mechoulam R, Braun P, Gaoni Y, J. Am. Chem. Soc. 1967 89 4552
15. Mechoulam R, Braun P, Gaoni Y, J. Am. Chem. Soc. 1972 94 6159
16. Fahrenholtz K E., Lurk M, Kierstead R W., J. Am. Chem. Soc. 1966 88 2079
17. Fahrenholtz K E., Lurk M, Kierstead R W., J. Am. Chem. Soc. 1967 89 5934
18. Chan T H., Chaly T, Tetrahedron 1982 23 2935
19. Rickards R W., Ronneberg H, J. Org. Chem. 1984 49 572
20. Childers W E. Jr., Pinnick H W., J. Org. Chem. 1984 49 5276
21. Malkov A V., Koovsky P, Collect. Czech. Chem. Commun. 2001 66 1257
22. William A D., Kobayashi Y, J. Org. Chem. 2002 67 8771
23. William A D., Kobayashi Y, Org. Lett. 2001 3 2017
24. Evans D A., Barnes D M., Johnson J S., Lectka T, Matt P V., Millier S J., Murry J A., Norcross R D., Shaughnessy E A., Campos K R., J. Am. Chem. Soc. 1999 121 7582
25. Trost B M., Dogra K, Org. Lett. 2007 9 861
26. Song Y, Hwang S, Gong P, Kim D, Kim S, Org. Lett. 2008 10 269
27. Ballerini E, Minuti L, Piermatti O, Pizzo F, J. Org. Chem. 2009 74 4311
28. Taylor E C., Lenard K, Shvo Y, J. Am. Chem. Soc. 1966 88; 367
29. Petrzika T, Sikemeier C, Helv. Chim. Acta. 1967 50 1416
30. Handrick G R., Razdan R K., Uliss D B., Dalzell H C., Boger E, J. Org. Chem. 1997 42 2563
31. Kowalski C J., Lal G S., J. Am. Chem. Soc. 1988 110 3693
32. Qi L, Yamamoto N, Meijler M M., Altobell L J. III, Koob G F., Wirsching P, Janda K D., J. Med. Chem. 2005 48 7389
33. N2 reaction, see
34. Marshall J A., Chem. Rev. 1989 89 1503
35. Li L, Rayabarapu D K., Nandi M, Cheng C, Org. Lett. 2003 5 1621
36. Smith A B. III, Pitram S M., Gaunt M J., Kozmin S A., J. Am. Chem. Soc. 2002; 124 14516
37. Spino C, Beaulieu C, Lafreniére J, J. Org. Chem. 2000 65 7091
38. Wang X, Wu Y, Jiang S, Singh G, J. Org. Chem. 2000 65 8146
39. Xie C, Nowak P, Kishi Y, Org. Lett. 2002 4 4427
40. Iura Y, Sugahara T, Ogasawara K, Org. Lett. 2001 3 291
41. Harrington-Frost N, Leuser H, Calaza M I., Kneisel F F., Knochel P, Org. Lett. 2003 5 2111
42. Soorukram D, Knochel P, Org. Lett. 2004 6 2409
43. Calaza M I., Yang X, Soorukram D, Knochel P, Org. Lett. 2004 6 529
44. Marino J P., Hatanaka N, J. Org. Chem. 1979 44 4467
45. Wender P A., Erhardt J M., Letendre L J., [nl]J. Am. Chem. Soc. 1981 103 2114
46. Marino J P., Jaén J C., J. Am. Chem. Soc. 1982 104 3165
47. Marino J P., Kelly M G., J. Org. Chem. 1981 46 4389
48. Marino J P., Pradilla F, Laborde E, J. Org. Chem. 1987 52 4898
49. Clive D L. J., Wickens P L., Silva G V. J., J. Org. Chem. 1995; 60 5532
50. Wang Q L., Huang Q G., Chen B, Lu J P., Wang H, She X G., Pan X F., Angew. Chem. Int. Ed. 2006 22 3651
51. Huang Q G., Wang Q L., Zheng J Y., Zhang J Y., Pan X F., She X G., Tetrahedron 2007 63 1014
52. Lipshutz B H., Wilhelm R S., Kozlowski J A., Parker D J., J. Org. Chem. 1984 49 3928
53. Barton D H. R., McCombie S W., J. Chem. Soc., Perkin Trans. 1 1975 16 1574
54. Barton D H. R., Lobberding D C. A., Zard S Z., Tetrahedron 1986 42 2329
55. For a review see:, Crich D, Quintero L, Chem. Rev. 1989 89 1413