Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2010(11): 1766-1770
DOI: 10.1055/s-0029-1218732
DOI: 10.1055/s-0029-1218732
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkTotal Synthesis of (-)-Δ8-trans-Tetrahydrocannabinol
Further Information
Received
21 January 2010
Publication Date:
12 April 2010 (online)
Publication History
Publication Date:
12 April 2010 (online)

Abstract
(-)-Δ8-trans-Tetrahydrocannabinol was synthesized with high regio- and stereoselectivity through SN2′ addition of an arylcyanocuprate to the optically pure enol silyl ether of α,β-epoxycyclohexanone.
Key words
addition reactions - heterocycles - tetrahydrocannabinol - deoxygenation - stereoselective synthesis
- 1a
Taylor EC.Lenard K.Shvo Y. J. Am. Chem. Soc. 1966, 88: 367 - 1b
Fahrenholtz KE.Lurie M.Kierstead RW. J. Am. Chem. Soc. 1967, 89: 5934 - 1c
Binder M.Franke I.Schmidt B.Dietrich W. Helv. Chim. Acta 1982, 65: 807 - 2a
Gernard CM.Mollereau C.Vassart G.Parmentier M. Biochem. J. 1991, 279: 129 - 2b
Skaper SD.Buriani A.Dal Toso R.Petrelli L.Romamello S.Faca L.Leon A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93: 3984 - 2c
Matsuda LA.Lolait SJ.Brownstein MJ.Young AC.Bonner TI. Nature (London, U.K.) 1990, 346: 61 - 2d
Munro S.Thomas KL.Abu-shaar M. Nature (London, U.K.) 1993, 365: 61 - 3
Di Marzo V.Goparaju SK.Wang L.Liu J.Batkai S.Jarai Z.Fezza F.Miura GI.Palmiter RD.Sugiuram T.Kunos G. Nature (London, U.K.) 2001, 410: 822 - 4
Parolaro D.Massi P.Rubino T.Monti E. Prostaglandins, Leukotrienes Essent. Fatty Acids 2002, 66: 319 - 5
Palmer SL.Thakur GA.Makriyannis A. Chem. Phys. Lipids 2002, 121: 3 - 6
Porcella A.Maxia C.Gessa GL.Pani L. Eur. J. Neurosci. 2001, 13: 409 - 7
Chien FY.Wang RF.Mittag TW.Podos SM. Arch. Ophthalmol. 2003, 121: 87 - For selected examples, see:
- 8a
Mechoulam R.Gaoni Y.
J. Am. Chem. Soc. 1965, 87: 3273 - 8b
Mechoulam R.Braun P.Gaoni Y. J. Am. Chem. Soc. 1967, 89: 4552 - 8c
Mechoulam R.Braun P.Gaoni Y. J. Am. Chem. Soc. 1972, 94: 6159 - 8d
Fahrenholtz KE.Lurk M.Kierstead RW. J. Am. Chem. Soc. 1966, 88: 2079 - 8e
Fahrenholtz KE.Lurk M.Kierstead RW. J. Am. Chem. Soc. 1967, 89: 5934 - 8f
Chan TH.Chaly T. Tetrahedron 1982, 23: 2935 - 8g
Rickards RW.Ronneberg H. J. Org. Chem. 1984, 49: 572 - 8h
Childers WE.Pinnick HW. J. Org. Chem. 1984, 49: 5276 - 8i
Malkov AV.Koovsky P. Collect. Czech. Chem. Commun. 2001, 66: 1257 - 8j
William AD.Kobayashi Y. J. Org. Chem. 2002, 67: 8771 - 8k
William AD.Kobayashi Y. Org. Lett. 2001, 3: 2017 - 8l
Evans DA.Barnes DM.Johnson JS.Lectka T.Matt PV.Millier SJ.Murry JA.Norcross RD.Shaughnessy EA.Campos KR. J. Am. Chem. Soc. 1999, 121: 7582 - 8m
Trost BM.Dogra K. Org. Lett. 2007, 9: 861 - 8n
Song Y.Hwang S.Gong P.Kim D.Kim S. Org. Lett. 2008, 10: 269 - 8o
Ballerini E.Minuti L.Piermatti O.Pizzo F. J. Org. Chem. 2009, 74: 4311 - 9a
Taylor EC.Lenard K.Shvo Y. J. Am. Chem. Soc. 1966, 88; 367 - 9b
Petrzika T.Sikemeier C. Helv. Chim. Acta. 1967, 50: 1416 - 9c
Handrick GR.Razdan RK.Uliss DB.Dalzell HC.Boger E. J. Org. Chem. 1997, 42: 2563 - 9d
Kowalski CJ.Lal GS. J. Am. Chem. Soc. 1988, 110: 3693 - 9e
Qi L.Yamamoto N.Meijler MM.Altobell LJ.Koob GF.Wirsching P.Janda KD. J. Med. Chem. 2005, 48: 7389 - For a review of the SN2′ reaction, see:
- 10a
Marshall JA. Chem. Rev. 1989, 89: 1503 - For recent references on the SN2′ reaction, see:
- 10b
Li L.Rayabarapu DK.Nandi M.Cheng C. Org. Lett. 2003, 5: 1621 - 10c
Smith AB.Pitram SM.Gaunt MJ.Kozmin SA. J. Am. Chem. Soc. 2002, ; 124: 14516 - 10d
Spino C.Beaulieu C.Lafreniére J. J. Org. Chem. 2000, 65: 7091 - 10e
Wang X.Wu Y.Jiang S.Singh G. J. Org. Chem. 2000, 65: 8146 - 10f
Xie C.Nowak P.Kishi Y. Org. Lett. 2002, 4: 4427 - 10g
Iura Y.Sugahara T.Ogasawara K. Org. Lett. 2001, 3: 291 - 10h
Harrington-Frost N.Leuser H.Calaza MI.Kneisel FF.Knochel P. Org. Lett. 2003, 5: 2111 - 10i
Soorukram D.Knochel P. Org. Lett. 2004, 6: 2409 - 10j
Calaza MI.Yang X.Soorukram D.Knochel P. Org. Lett. 2004, 6: 529 - 11a
Marino JP.Hatanaka N. J. Org. Chem. 1979, 44: 4467 - 11b
Wender PA.Erhardt JM.Letendre LJ.
J. Am. Chem. Soc. 1981, 103: 2114 - 11c
Marino JP.Jaén JC. J. Am. Chem. Soc. 1982, 104: 3165 - 11d
Marino JP.Kelly MG. J. Org. Chem. 1981, 46: 4389 - 11e
Marino JP.Pradilla F.Laborde E. J. Org. Chem. 1987, 52: 4898 - 11f
Clive DLJ.Wickens PL.Silva GVJ. J. Org. Chem. 1995, ; 60: 5532 - 12a
Wang QL.Huang QG.Chen B.Lu JP.Wang H.She XG.Pan XF. Angew. Chem. Int. Ed. 2006, 22: 3651 - 12b
Huang QG.Wang QL.Zheng JY.Zhang JY.Pan XF.She XG. Tetrahedron 2007, 63: 1014 - 13
Lipshutz BH.Wilhelm RS.Kozlowski JA.Parker DJ. J. Org. Chem. 1984, 49: 3928 - 14a
Barton DHR.McCombie SW. J. Chem. Soc., Perkin Trans. 1 1975, 16: 1574 - 14b
Barton DHR.Lobberding DCA.Zard SZ. Tetrahedron 1986, 42: 2329 - 14c For a review see:
Crich D.Quintero L. Chem. Rev. 1989, 89: 1413