SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 4, 2008, Pages 535-538

Diastereoselective tandem Diels-Alder macrocyclizations starting from sorbyl or sorboyl derivatives

(2) Banert, Klaus a Schumann, Patrick a

a CHEMNITZ UNIVERSITY OF TECHNOLOGY (Germany)

Author keywords

1,2,4 triazoline 3,5 dione; Diastereoselectivity; Diels Alder; Macrocycles; Sorbyl and sorboyl derivatives

Indexed keywords

SORBOYL DERIVATIVE; SORBYL DERIVATIVE; THROMBIN INHIBITOR; TRIAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DIASTEREOISOMER; DIELS ALDER REACTION; DRUG SYNTHESIS;

EID: 41049103984 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1032083 Document Type: Article

Times cited : (5)

References (36)

1
- 84962105974
- Diels, O.; Alder, K. Justus Liebigs Ann. Chem. 1928, 460, 98.
- (1928) Justus Liebigs Ann. Chem , vol.460 , pp. 98
- Diels, O.¹ Alder, K.²

2
- 0000479137
- (a) Winkler, J. Chem. Rev. 1996, 96, 167.
- (1996) Chem. Rev , vol.96 , pp. 167
- Winkler, J.¹

3
- 41049112869
- (b) Wald, K.; Wamhoff, H. Chem. Ber. 1978, 111, 3519.
- (1978) Chem. Ber , vol.111 , pp. 3519
- Wald, K.¹ Wamhoff, H.²

4
- 0036259981
- (a) Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem. Int. Ed. 2002, 41, 1668.
- (2002) Angew. Chem. Int. Ed , vol.41 , pp. 1668
- Nicolaou, K.C.¹ Snyder, S.A.² Montagnon, T.³ Vassilikogiannakis, G.⁴

5
- 0000104235
- (b) Thomas, E. J. Acc. Chem. Res. 1991, 24, 229.
- (1991) Acc. Chem. Res , vol.24 , pp. 229
- Thomas, E.J.¹

6
- 3743149516
- (a) Reinecke, M.; Ritter, H. J. J. Macromol. Sci., Pure Appl. Chem. 1997, 34, 2321.
- (1997) J. Macromol. Sci., Pure Appl. Chem , vol.34 , pp. 2321
- Reinecke, M.¹ Ritter, H.J.²

7
- 33745007109
- (b) Teramoto, N.; Arai, Y.; Shibata, M. Carbohydr. Polym. 2006, 64, 78.
- (2006) Carbohydr. Polym , vol.64 , pp. 78
- Teramoto, N.¹ Arai, Y.² Shibata, M.³

8
- 84943051694
- (a) Sauer, J. Angew. Chem., Int. Ed. Engl. 1967, 6, 16.
- (1967) Angew. Chem., Int. Ed. Engl , vol.6 , pp. 16
- Sauer, J.¹

9
- 0342713055
- (b) Sauer, J.; Sustmann, R. Angew. Chem., Int. Ed. Engl. 1980, 19, 779.
- (1980) Angew. Chem., Int. Ed. Engl , vol.19 , pp. 779
- Sauer, J.¹ Sustmann, R.²

10
- 37049076286
- (c) Craig, D. Chem. Soc. Rev. 1987, 16, 187.
- (1987) Chem. Soc. Rev , vol.16 , pp. 187
- Craig, D.¹

11
- 27544477652
- (a) Dockendorff, C.; Sahli, S.; Olsen, M.; Milhau, L.; Lautens, M. J. Am. Chem. Soc. 2005, 127, 15028.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 15028
- Dockendorff, C.¹ Sahli, S.² Olsen, M.³ Milhau, L.⁴ Lautens, M.⁵

12
- 85037516107
- (b) Ward, D. E.; Saeed Abaee, M. Org. Lett. 2000, 24, 3937.
- (2000) Org. Lett , vol.24 , pp. 3937
- Ward, D.E.¹ Saeed Abaee, M.²

13
- 29344456609
- (c) Käss, S.; Gregor, T.; Kersting, B. Angew. Chem. Int. Ed. 2006, 45, 101.
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 101
- Käss, S.¹ Gregor, T.² Kersting, B.³

14
- 0013011923
- (d) Itami, K.; Nokami, T.; Yoshida, J. Adv. Synth. Catal. 2002, 344, 441.
- (2002) Adv. Synth. Catal , vol.344 , pp. 441
- Itami, K.¹ Nokami, T.² Yoshida, J.³

15
- 0000324021
- (e) Franck, R. W.; Argade, S.; Subramaniam, C. S.; Frechet, D. M. Tetrahedron Lett. 1985, 26, 3187.
- (1985) Tetrahedron Lett , vol.26 , pp. 3187
- Franck, R.W.¹ Argade, S.² Subramaniam, C.S.³ Frechet, D.M.⁴

16
- 0036900511
- (f) Adam, W.; Bosio, S. G.; Degen, H.-G.; Krebs, O.; Stalke, D.; Schumacher, D. Eur. J. Org. Chem. 2002, 3944.
- (2002) Eur. J. Org. Chem , pp. 3944
- Adam, W.¹ Bosio, S.G.² Degen, H.-G.³ Krebs, O.⁴ Stalke, D.⁵ Schumacher, D.⁶

17
- 0027997763
- (g) Nojima, K.; Isogami, C.; Kobashi, M. Jpn. J. Toxicol. Environ. Health 1994, 40, 467.
- (1994) Jpn. J. Toxicol. Environ. Health , vol.40 , pp. 467
- Nojima, K.¹ Isogami, C.² Kobashi, M.³

18
- 33845279009
- (h) Tripathy, R.; Franck, R. W.; Onan, K. D. J. Am. Chem. Soc. 1988, 110, 3257.
- (1988) J. Am. Chem. Soc , vol.110 , pp. 3257
- Tripathy, R.¹ Franck, R.W.² Onan, K.D.³

19
- 0030907129
- (i) Khandelwal, G. D.; Wedzicha, B. L. Food Chem. 1997, 60, 237.
- (1997) Food Chem , vol.60 , pp. 237
- Khandelwal, G.D.¹ Wedzicha, B.L.²

20
- 37049078897
- (j) Fleming, I.; Sarkar, A. K.; Doyle, M. J.; Raithby, P. R. J. Chem. Soc., Perkin Trans. 1 1989, 2023.
- (1989) J. Chem. Soc., Perkin Trans. 1 , pp. 2023
- Fleming, I.¹ Sarkar, A.K.² Doyle, M.J.³ Raithby, P.R.⁴

21
- 41049111755
- US 6117896, 192934
- Qabar, M. N.; McMillan, M. K.; Kahn, M. S.; Tulinsky, J. E.; Ogbu, C. O.; Mathew, J. US 6117896, 1998; Chem. Abstr. 1998, 128, 192934.
- (1998) Chem. Abstr , vol.128
- Qabar, M.N.¹ McMillan, M.K.² Kahn, M.S.³ Tulinsky, J.E.⁴ Ogbu, C.O.⁵ Mathew, J.⁶

22
- 0000515321
- (a) White, J. D.; Sheldon, B. G. J. Org. Chem. 1981, 46, 2273.
- (1981) J. Org. Chem , vol.46 , pp. 2273
- White, J.D.¹ Sheldon, B.G.²

23
- 0025977675
- (b) Sheradsky, T.; Milvitskaya, J.; Pollak, I. E. Tetrahedron Lett. 1991, 32, 133.
- (1991) Tetrahedron Lett , vol.32 , pp. 133
- Sheradsky, T.¹ Milvitskaya, J.² Pollak, I.E.³

24
- 27144521210
- (c) Zapf, C. W.; Harrison, B. A.; Drahl, C.; Sorensen, E. J. Angew. Chem. Int. Ed. 2005, 44, 6533.
- (2005) Angew. Chem. Int. Ed , vol.44 , pp. 6533
- Zapf, C.W.¹ Harrison, B.A.² Drahl, C.³ Sorensen, E.J.⁴

25
- 0033529930
- (d) Sun, S.; Murray, W. V. J. Org. Chem. 1999, 64, 5941.
- (1999) J. Org. Chem , vol.64 , pp. 5941
- Sun, S.¹ Murray, W.V.²

26
- 0029148959
- (e) Ainsworth, P. J.; Craig, D.; Reader, J. C.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tedrahedron 1995, 51, 11601.
- (1995) Tedrahedron , vol.51 , pp. 11601
- Ainsworth, P.J.¹ Craig, D.² Reader, J.C.³ Slawin, A.M.Z.⁴ White, A.J.P.⁵ Williams, D.J.⁶

27
- 0001389375
- Reinecke, M.; Ritter, H. Macromol. Chem. Phys. 1994, 195, 2445.
- (1994) Macromol. Chem. Phys , vol.195 , pp. 2445
- Reinecke, M.¹ Ritter, H.²

28
- 0006633761
- Hertel, R.; Mattay, J.; Runsink, J. J. Am. Chem. Soc. 1991, 113, 657.
- (1991) J. Am. Chem. Soc , vol.113 , pp. 657
- Hertel, R.¹ Mattay, J.² Runsink, J.³

29
- 0032880084
- Zolfigol, M. A.; Mallakpour, S. E. Synth. Commun. 1999, 29, 4061.
- (1999) Synth. Commun , vol.29 , pp. 4061
- Zolfigol, M.A.¹ Mallakpour, S.E.²

30
- 84985520823
- Neises, B.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1978, 17, 522.
- (1978) Angew. Chem., Int. Ed. Engl , vol.17 , pp. 522
- Neises, B.¹ Steglich, W.²

31
- 0000509094
- Kim, T.; Mirafzal, G. A.; Liu, J.; Bauld, N. L. J. Am. Chem. Soc. 1993, 115, 7653.
- (1993) J. Am. Chem. Soc , vol.115 , pp. 7653
- Kim, T.¹ Mirafzal, G.A.² Liu, J.³ Bauld, N.L.⁴

32
- 84928700723
- Oppolzer, W.; Poli, G.; Kingma, A. J.; Starkemann, C.; Bernardinelli, G. Helv. Chim. Acta 1987, 70, 2201.
- (1987) Helv. Chim. Acta , vol.70 , pp. 2201
- Oppolzer, W.¹ Poli, G.² Kingma, A.J.³ Starkemann, C.⁴ Bernardinelli, G.⁵

33
- 41049102352
- Giesecke, H.; Merten, R.; Rottmaier, L. EP 44421, 1982; Chem. Abstr. 1982, 96, 1999701q.
- Giesecke, H.; Merten, R.; Rottmaier, L. EP 44421, 1982; Chem. Abstr. 1982, 96, 1999701q.

34
- 41049094571
- General Procedure for Macrocyclizations A flask is charged with CH2Cl2 (800-1400 ml) as a diluting agent. Dichloromethane often contains 2-methylbut-2-ene as a stabilizer which undergoes ene reaction when it is treated with TAD derivatives. Therefore, it must be removed before using larger amounts of CH2Cl2, e.g. by the addition of a few drops of bromine. Furthermore, the flask is equipped with two dropping funnels containing 15-50 mM solutions of bis-TAD 2 and bisdiene 1. Both solutions are simultaneously added dropwise at r.t. into the vigorously stirred solvent at such a rate that only a faint pink color can be observed (normally 3-5 h, After complete addition, the reaction mixture is concentrated in vacuo and chromatographed on silica gel to yield colorless solids. Spectroscopic Data of rac-3ac, rac-3ad, and meso-3ad rac-3ac both enantiomers, mp 1
- 2), 18.2 (q, CHMe).

35
- 0343537654
- Rádl, S. Adv. Heterocycl. Chem. 1997, 67, 119.
- (1997) Adv. Heterocycl. Chem , vol.67 , pp. 119
- Rádl, S.¹

36
- 41049105984
- A diluted solution of 1g (1 equiv) in CH2Cl2 was treated with 4-phenyl-1,2,4-triazoline-3,5-dione (0.8 equiv) in CH 2Cl2 at r.t. After evaporation of the solvent, NMR analysis of the crude product revealed only a mixture of 1g and the PTAD-sorbyl adduct, which was isolated by flash chromatography in 69% yield as a colorless solid, 5S,8S)-8-Methyl-1,3-dioxo-2-phenyl-2,3,5,8- tetrahydro-1H-[1,2,4]triazolo[1,2-a]pyridazin-5-yl]methyl (2E,4E)-hexa-2,4-dienoate (both enantiomers, mp (CH 2Cl2-acetone, 117°C IR (CDCl3, v, 1770 (w, 1712 (vs, C=O, 1426 (m, 1243 (m) cm-1. 1H NMR (400 MHz, CDCl3, CHCl3, 7.26 ppm, δ, 7.52 (m, 2 H, 3-PhCH, 7.46 (m, 2 H, 2-PhCH, 7.36 (tt, J, 7.2, 1.2 Hz, 1 H, 4-PhCH, 7.25 (dd, J, 15.2, 10.8 Hz, 1 H, CH, 6.04-6.20 (m, 2 H, CH, 5.92 ddd, J
- 4: C, 65.38; H, 5.76; N, 11.44. Found: C, 65.18; H, 5.94; N, 11.41.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.