SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 3, 2008, Pages 329-332

An approach to cannabinoids by radical cyclisation of 1,7-dienes using diethyl thiophosphite

(3) Healy, Mark P a Parsons, Andrew F b Rawlinson, James G T b

a GLAXOSMITHKLINE (United Kingdom)

b UNIVERSITY OF YORK (United Kingdom)

Author keywords

Addition reactions; Cyclisations; Ethers; Radical reactions; Substituent effects

Indexed keywords

ALKADIENE; CANNABINOID; CHROMAN DERIVATIVE; PHOSPHOROTHIOIC ACID; SALICYLALDEHYDE;

ADDITION REACTION; ARTICLE; CYCLIZATION; DRUG SYNTHESIS; METHODOLOGY; PRECURSOR;

EID: 39749186596 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1032049 Document Type: Article

Times cited : (10)

References (44)

1
- 0033918979
- (a) Fichera, M.; Cruciani, G.; Bianchi, A.; Musumarra, G. J. Med. Chem. 2000, 43, 2300.
- (2000) J. Med. Chem , vol.43 , pp. 2300
- Fichera, M.¹ Cruciani, G.² Bianchi, A.³ Musumarra, G.⁴

2
- 0019308268
- (b) Turner, C. E.; Elsohly, M. A.; Boeren, E. G. J. Nat. Prod. 1980, 43, 169.
- (1980) J. Nat. Prod , vol.43 , pp. 169
- Turner, C.E.¹ Elsohly, M.A.² Boeren, E.G.³

3
- 0034642492
- See for example: a
- See for example: (a) Keimowitz, A. R.; Martin, B. R.; Razdan, R. K.; Crocker, P. J.; Mascarella, S. W.; Thomas, B. F. J. Med. Chem. 2000, 43, 59.
- (2000) J. Med. Chem , vol.43 , pp. 59
- Keimowitz, A.R.¹ Martin, B.R.² Razdan, R.K.³ Crocker, P.J.⁴ Mascarella, S.W.⁵ Thomas, B.F.⁶

4
- 18444376760
- (b) Howlett, A. C.; Barth, F.; Bonner, T. I.; Cabral, G.; Casellas, P.; Devane, W. A.; Felder, C. C.; Herkenham, M.; Mackie, K.; Martin, B. R.; Pertwee, R. G. Pharmacol. Rev. 2002, 54, 161.
- (2002) Pharmacol. Rev , vol.54 , pp. 161
- Howlett, A.C.¹ Barth, F.² Bonner, T.I.³ Cabral, G.⁴ Casellas, P.⁵ Devane, W.A.⁶ Felder, C.C.⁷ Herkenham, M.⁸ Mackie, K.⁹ Martin, B.R.¹⁰ Pertwee, R.G.¹¹

5
- 28544452150
- (c) Salo, O. M. H.; Raitio, K. H.; Savinainen, J. R.; Nevalainen, T.; Lahtela-Kakkonen, M.; Laitinen, J. T.; Järvinen, T.; Poso, A. J. Med. Chem. 2005, 48, 7166.
- (2005) J. Med. Chem , vol.48 , pp. 7166
- Salo, O.M.H.¹ Raitio, K.H.² Savinainen, J.R.³ Nevalainen, T.⁴ Lahtela-Kakkonen, M.⁵ Laitinen, J.T.⁶ Järvinen, T.⁷ Poso, A.⁸

6
- 0032568420
- For some previous synthetic approaches to cannabinoids, see: a
- For some previous synthetic approaches to cannabinoids, see: (a) Papahatjis, D. P.; Kourouli, T.; Abadji, V.; Goutopoulos, A.; Makriyannis, A. J. Med. Chem. 1998, 41, 1195.
- (1998) J. Med. Chem , vol.41 , pp. 1195
- Papahatjis, D.P.¹ Kourouli, T.² Abadji, V.³ Goutopoulos, A.⁴ Makriyannis, A.⁵

7
- 0038493770
- (b) Papahatjis, D. P.; Nikas, S. P.; Kourorli, T.; Chari, R.; Xu, W.; Pertwee, R. G.; Makriyannis, A. J. Med. Chem. 2003, 46, 3221.
- (2003) J. Med. Chem , vol.46 , pp. 3221
- Papahatjis, D.P.¹ Nikas, S.P.² Kourorli, T.³ Chari, R.⁴ Xu, W.⁵ Pertwee, R.G.⁶ Makriyannis, A.⁷

8
- 0346993609
- (c) Sun, H.; Mahadevan, A.; Razdan, R. K. Tetrahedron Lett. 2004, 45, 615.
- (2004) Tetrahedron Lett , vol.45 , pp. 615
- Sun, H.¹ Mahadevan, A.² Razdan, R.K.³

9
- 0037428014
- (d) Chu, C.; Ramamurthy, A.; Makriyannis, A.; Tius, M. A. J. Org. Chem. 2003, 68, 55.
- (2003) J. Org. Chem , vol.68 , pp. 55
- Chu, C.¹ Ramamurthy, A.² Makriyannis, A.³ Tius, M.A.⁴

10
- 0033603850
- (e) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; von Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582.
- (1999) J. Am. Chem. Soc , vol.121 , pp. 7582
- Evans, D.A.¹ Barnes, D.M.² Johnson, J.S.³ Lectka, T.⁴ von Matt, P.⁵ Miller, S.J.⁶ Murry, J.A.⁷ Norcross, R.D.⁸ Shaughnessy, E.A.⁹ Campos, K.R.¹⁰

11
- 23044449376
- (f) Lesch, B.; Toräng, J.; Nieger, M.; Bräse, S. Synthesis 2005, 1888.
- (2005) Synthesis , pp. 1888
- Lesch, B.¹ Toräng, J.² Nieger, M.³ Bräse, S.⁴

12
- 34447252632
- (g) Nikas, S. P.; Thakur, G. A.; Parrish, D.; Alapafuja, S. O.; Huestis, M. A.; Makriyannis, A. Tetrahedron 2007, 63, 8112.
- (2007) Tetrahedron , vol.63 , pp. 8112
- Nikas, S.P.¹ Thakur, G.A.² Parrish, D.³ Alapafuja, S.O.⁴ Huestis, M.A.⁵ Makriyannis, A.⁶

13
- 0034609803
- Mahadevan, A.; Siegel, C.; Martin, B. R.; Abood, M. E.; Beletskaya, I.; Razdan, R. K. J. Med. Chem. 2000, 43, 3778.
- (2000) J. Med. Chem , vol.43 , pp. 3778
- Mahadevan, A.¹ Siegel, C.² Martin, B.R.³ Abood, M.E.⁴ Beletskaya, I.⁵ Razdan, R.K.⁶

14
- 33645093416
- For related addition reactions of phosphorus-centred radicals, see: a
- For related addition reactions of phosphorus-centred radicals, see: (a) Jessop, C. M.; Parsons, A. F.; Routledge, A.; Irvine, D. J. Eur. J. Org. Chem. 2006, 1547.
- (2006) Eur. J. Org. Chem , pp. 1547
- Jessop, C.M.¹ Parsons, A.F.² Routledge, A.³ Irvine, D.J.⁴

15
- 0037433936
- (b) Jessop, C. M.; Parsons, A. F.; Routledge, A.; Irvine, D. Tetrahedron Lett. 2003, 44, 479.
- (2003) Tetrahedron Lett , vol.44 , pp. 479
- Jessop, C.M.¹ Parsons, A.F.² Routledge, A.³ Irvine, D.⁴

16
- 2942534474
- (c) Jessop, C. M.; Parsons, A. F.; Routledge, A.; Irvine, D. J. Tetrahedron Lett. 2004, 45, 5095.
- (2004) Tetrahedron Lett , vol.45 , pp. 5095
- Jessop, C.M.¹ Parsons, A.F.² Routledge, A.³ Irvine, D.J.⁴

17
- 11844280968
- (d) Cho, D. H.; Jang, D. O. Synlett 2005, 59.
- (2005) Synlett , pp. 59
- Cho, D.H.¹ Jang, D.O.²

18
- 33646241793
- (e) Hunt, T. A.; Parsons, A. F.; Pratt, R. J. Org. Chem. 2006, 71, 3656.
- (2006) J. Org. Chem , vol.71 , pp. 3656
- Hunt, T.A.¹ Parsons, A.F.² Pratt, R.³

19
- 17944370091
- (f) Montchamp, J.-L. J. Organomet. Chem. 2005, 690, 2388.
- (2005) J. Organomet. Chem , vol.690 , pp. 2388
- Montchamp, J.-L.¹

20
- 26844495597
- (g) Leca, D.; Fensterbank, L.; Lacôte, E.; Malacria, M. Chem. Soc. Rev. 2005, 34, 858.
- (2005) Chem. Soc. Rev , vol.34 , pp. 858
- Leca, D.¹ Fensterbank, L.² Lacôte, E.³ Malacria, M.⁴

21
- 28844444993
- (h) Parsons, A. F.; Sharpe, D. J.; Taylor, P. Synlett 2005, 2981.
- (2005) Synlett , pp. 2981
- Parsons, A.F.¹ Sharpe, D.J.² Taylor, P.³

22
- 28844438922
- (i) Hunt, T.; Parsons, A. F.; Pratt, R. Synlett 2005, 2978.
- (2005) Synlett , pp. 2978
- Hunt, T.¹ Parsons, A.F.² Pratt, R.³

23
- 17844371929
- (j) Healy, M. P.; Parsons, A. F.; Rawlinson, J. G. T. Org. Lett. 2005, 7, 1597.
- (2005) Org. Lett , vol.7 , pp. 1597
- Healy, M.P.¹ Parsons, A.F.² Rawlinson, J.G.T.³

24
- 33947603435
- (k) Carta, P.; Puljic, N.; Robert, C.; Dhimane, A.-L.; Fensterbank, L.; Lacote, E.; Malacria, M. Org. Lett. 2007, 9, 1061.
- (2007) Org. Lett , vol.9 , pp. 1061
- Carta, P.¹ Puljic, N.² Robert, C.³ Dhimane, A.-L.⁴ Fensterbank, L.⁵ Lacote, E.⁶ Malacria, M.⁷

25
- 29244460056
- For complementary 6-exo-trig radical cyclisation approaches to tetrahydropyrans, see: (a) Lee, E. Pure Appl. Chem. 2005, 77, 2073.
- For complementary 6-exo-trig radical cyclisation approaches to tetrahydropyrans, see: (a) Lee, E. Pure Appl. Chem. 2005, 77, 2073.

26
- 23444450902
- (b) Hiramatsu, N.; Takahashi, N.; Noyori, R.; Mori, Y. Tetrahedron 2005, 61, 8589.
- (2005) Tetrahedron , vol.61 , pp. 8589
- Hiramatsu, N.¹ Takahashi, N.² Noyori, R.³ Mori, Y.⁴

27
- 3042672829
- (c) Hartung, J.; Gottwald, T. Tetrahedron Lett. 2004, 45, 5619.
- (2004) Tetrahedron Lett , vol.45 , pp. 5619
- Hartung, J.¹ Gottwald, T.²

28
- 0030857706
- (d) Evans, P. A.; Roseman, J. D. Tetrahedron Lett. 1997, 38, 5249.
- (1997) Tetrahedron Lett , vol.38 , pp. 5249
- Evans, P.A.¹ Roseman, J.D.²

29
- 0000284117
- (e) Leeuwenburgh, M. A.; Litjens, R. E. J. N.; Codée, J. D. C.; Overkleeft, H. S.; van der Marel, G. A.; van Boom, J. H. Org. Lett. 2000, 2, 1275.
- (2000) Org. Lett , vol.2 , pp. 1275
- Leeuwenburgh, M.A.¹ Litjens, R.E.J.N.² Codée, J.D.C.³ Overkleeft, H.S.⁴ van der Marel, G.A.⁵ van Boom, J.H.⁶

30
- 0000545082
- (f) Burke, S. D.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 2335.
- (1991) J. Am. Chem. Soc , vol.113 , pp. 2335
- Burke, S.D.¹ Rancourt, J.²

31
- 39749175982
- All new compounds gave consistent spectral and high resolution mass spectroscopic data
- All new compounds gave consistent spectral and high resolution mass spectroscopic data.

32
- 37049067687
- See for example: a
- See for example: (a) Journet, M.; Lacôte, E.; Malacria, M. J. Chem. Soc., Chem. Commun. 1994, 461.
- (1994) J. Chem. Soc., Chem. Commun , pp. 461
- Journet, M.¹ Lacôte, E.² Malacria, M.³

33
- 33644768294
- (b) Maulide, N.; Markov, I. E. Chem. Commun. 2006, 1200.
- (2006) Chem. Commun , pp. 1200
- Maulide, N.¹ Markov, I.E.²

34
- 39749108517
- Z)-1-(2-Methylpent-3-en-2-yloxy)-2-vinylbenzene (13a, yellow oil. IR (CDCl3, 3085, 3065, 2958, 2927, 1603, 1487, 1456, 1439, 1377, 1174, 1120 cm-1. 1H NMR (400 MHz, CDCl3, δ, 6.80-7.70 (m, 4 H, 4 x ArCH, 7.10 (dd, J, 17.5, 11.0 Hz, 1 H, CH=CHAHB, 5.72 (dd, J, 17.5 1.5 Hz, 1 H, CH=CHAHB, 5.64 (dq, J, 12.0, 1.5 Hz, 1 H, CH=CHMe, 5.54 (dq, J, 12.0, 7.0 Hz, 1 H, CH=CHMe, 5.22 (dd, J, 11.0, 1.5 Hz, 1 H, CH=CH AHB, 1.70 (d, J, 7.0 Hz, 3 H, Me, 1.53 (s, 6 H, MeCMe, 13C NMR (100 MHz, CDCl3, δ, 153.5 (ArCO, 135.1, 132.0, 128.4, 127.4, 126.1, 120.7, 118.1 (4 x ArCH, CH=CHAHB, CH=CHMe, 128.6 (ArCCH=C, 113.7 (CH=CHAHB, 79.4 MeCMe, 28
- +]: 203.1436; found: 203.1436.

35
- 39749189818
- Synthesis of O,O-Diethyl (3-Ethyl-2,2-dimethyl-3,4- dihydro-2H-chromen-4-yl)methylphosphonothioate (14a, 1,7-Diene 13a (0.150 g, 0.74 mmol, 1 equiv, diethyl thiophosphite (0.114 g, 0.74 mmol, 1 equiv) and AIBN (0.097 g, 0.59 mmol, 0.8 equiv, 1 portion) were heated to reflux in degassed cyclohexane (20 mL) overnight. After cooling to r.t, the solvent was evaporated and purification of the crude product by column chromatography (silica, petrol) afforded 14a (0.073 g, 28, as a colourless oil, as an inseparable 1:1 mixture of cis- and trans-diastereoisomers as indicated by the 1H NMR spectrum. IR (CH2Cl2, 3055, 2983, 2937, 2904, 2879, 1606, 1581, 1487, 1452, 1387, 1371, 1302, 1261, 1225, 1159, 1026 cm-1. 1H NMR (400 MHz, CDCl3; both diastereoisomers, δ, 7.40, 7.29 (2 x d, 2 x J, 8.0 Hz, 1 H, ArCH, 7.11, 7.09 2 x t, 2 x J, 8.0 Hz
- +]: 357.1653; found: 357.1652.

36
- 0034678011
- For other examples of 6-exo cyclisations of benzylic radicals, see: (a) Studer, A. Angew Chem. Int. Ed. 2000, 1108.
- For other examples of 6-exo cyclisations of benzylic radicals, see: (a) Studer, A. Angew Chem. Int. Ed. 2000, 1108.

37
- 2342488214
- (b) Pattenden, G.; Reddy, L. K.; Walter, A. Tetrahedron Lett. 2004, 45, 4027.
- (2004) Tetrahedron Lett , vol.45 , pp. 4027
- Pattenden, G.¹ Reddy, L.K.² Walter, A.³

38
- 0037288245
- (c) Binot, G.; Quiclet-Sire, B.; Saleh, T.; Zard, S. Z. Synlett 2003, 382.
- (2003) Synlett , pp. 382
- Binot, G.¹ Quiclet-Sire, B.² Saleh, T.³ Zard, S.Z.⁴

39
- 0343043242
- Resonance-stabilised radicals are known to undergo reversible cyclisations. See for example: (a) Walling, C.; Cioffari, A. J. Am. Chem. Soc. 1972, 94, 6064.
- Resonance-stabilised radicals are known to undergo reversible cyclisations. See for example: (a) Walling, C.; Cioffari, A. J. Am. Chem. Soc. 1972, 94, 6064.

40
- 0000041227
- (b) Julia, M. Acc. Chem. Res. 1971, 4, 386.
- (1971) Acc. Chem. Res , vol.4 , pp. 386
- Julia, M.¹

41
- 33748905837
- (c) Julia, M. Pure Appl. Chem. 1974, 40, 553.
- (1974) Pure Appl. Chem , vol.40 , pp. 553
- Julia, M.¹

42
- 39749150153
- Synthesis of Methyl 2-{4, Diethoxyphosphorothioyl)methyl]-2,2- dimethyl-3,4-dihydro-2H-chromen-3-yl}acetate (14c, 1,7-Diene 13c (0.250 g, 1.02 mmol, 1 equiv, diethyl thiophosphite (0.782 g, 5.08 mmol, 5 equiv) and AIBN (0.042 g, 0.25 mmol, 0.25 equiv, 5 portions, 1 h between additions) were heated to reflux in anhyd degassed THF (20 mL) overnight. After cooling to r.t, the solvent was evaporated and excess diethyl thiophosphite was removed by distillation (75°C/3 mmHg, Purification of the residue by column chromatography (silica; PE-Et2O, 9:1) afforded 14c (0.221 g, 54, as a yellow oil. IR (CH2Cl2, 2982, 2953, 2853, 1735, 1608, 1582, 1488, 1453, 1437, 1388, 1372, 1302, 1249, 1228, 1170, 1138, 1116, 1098, 1026 cm-1. 1H NMR (400 MHz, CDCl3, δ, 7.48 (d, J, 7.5 Hz, 1 H, ArCH, 7.11 (t, J, 7.5 Hz, 1 H, ArCH, 6.90 t, J, 7.5 Hz, 1 H, ArCH, 6.76
- +]: 401.1552; found: 401.1551.

43
- 39749083081
- 4-(2,2-Diphenylvinyl)-3-ethyl-2,2-dimethylchromane (15, colourless oil (6.5:1 mixture of diastereoisomers, IR (CH2Cl 2, 3019, 2958, 2931, 1598, 1581, 1484, 1451, 1386, 1302, 1148, 1030 cm-1. 1H NMR (400 MHz, CDCl3; both diastereoisomers, δ, 7.20-7.42 (m, 11 H, 11 x ArCH, 7.11 (t, J, 7.0 Hz, 1 H, ArCH, 6.85 (t, J, 7.0 Hz, 1 H, ArCH, 6.77 (d, J, 7.0 Hz, 1 H, ArCH, 6.29, 5.95 (2 x d, J, 2 x 10.5 Hz, 1 H, cis-C=CH and trans-C=CH, 3.42 (app. t, J, 10.5 Hz, 1 H, CHCH=C, 1.54 (dt, J, 10.5, 4.5 Hz, 1 H, CHCH 2Me, 0.98, 1.42 (2 x s, 2 x 3 H, MeCMe, 1.20-1.40 (m, 2 H, CH2Me, 0.80-0.92 (m, 3 H, CH2Me, 13C NMR (100 MHz, CDCl3; both diastereoisomers, δ, 153.1 (ArCO, 143.2, 142.3, 139.8 3 x ArC, 131.1, 2 x 129.6, 2 x 128.4, 2 x 128.2, 127.8, 2 x 127.3
- +]: 369.2218; found: 369.2217.

44
- 1242341174
- For a related cyclisation, see
- For a related cyclisation, see: Samarat, A.; Landais, Y.; Amri, H. Tetrahedron Lett. 2004, 45, 2049.
- (2004) Tetrahedron Lett , vol.45 , pp. 2049
- Samarat, A.¹ Landais, Y.² Amri, H.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.