SCOPUS 정보 검색 플랫폼

Volumn , Issue 3, 2007, Pages 403-406

Synthesis of novel polyhydroxylated tetrahydropyranopyrroles

(7) Naud, Sébastien a Pipelier, Muriel a Chaumette, Christophe a Viault, Guillaume a Huet, François b Legoupy, Stéphanie b Dubreuil, Didier a

a UNIVERSITÉ DE NANTES (France)

b UNIVERSITÉ DU MAINE (France)

Author keywords

pyrones; Cycloadditions; Pyridazines; Pyrroles; Ring contractions

Indexed keywords

3 BUTYL 4 HYDROXY 2 METHOXYCARBONYL 7 OXO 5 (1',2',3' TRIHYDROXYPROP 1' YL) 1,4,5,7 TETRAHYDROPYRANO[3,4 B]PYRROLE; PYRIDAZINE DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DIELS ALDER REACTION; HYDROXYLATION; LACTONIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 33847339727 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-968030 Document Type: Article

Times cited : (7)

References (21)

1
- 0001375672
- Mereyala, H. B.; Joe, M. Curr. Med. Chem. 2001, 1, 293.
- (2001) Curr. Med. Chem , vol.1 , pp. 293
- Mereyala, H.B.¹ Joe, M.²

2
- 0021921867
- (a) Hoffmann, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1985, 24, 94.
- (1985) Angew. Chem., Int. Ed. Engl , vol.24 , pp. 94
- Hoffmann, H.M.R.¹ Rabe, J.²

3
- 25444465477
- (b) Ramana, C. V.; Srinivas, B.; Puranik, V. G.; Gurjar, M. K. J. Org. Chem. 2005, 70, 8216.
- (2005) J. Org. Chem , vol.70 , pp. 8216
- Ramana, C.V.¹ Srinivas, B.² Puranik, V.G.³ Gurjar, M.K.⁴

4
- 29744452186
- Boruwa, J.; Barua, N. C. Tetrahedron 2006, 62, 1193.
- (2006) Tetrahedron , vol.62 , pp. 1193
- Boruwa, J.¹ Barua, N.C.²

5
- 0024953609
- Alkofahi, A.; Ma, W.-W.; McKenzie, A. T.; Byrn, S. R.; McLaughlin, J. L. J. Nat. Prod. 1989, 52, 1371.
- (1989) J. Nat. Prod , vol.52 , pp. 1371
- Alkofahi, A.¹ Ma, W.-W.² McKenzie, A.T.³ Byrn, S.R.⁴ McLaughlin, J.L.⁵

6
- 0010384048
- Fang, X.-P.; Anderson, J. E.; Chang, C.-J.; Fanwick, P. E.; McLaughlin, J. L. J. Chem. Soc., Perkin Trans. 1 1990, 1655.
- (1990) J. Chem. Soc., Perkin Trans. 1 , pp. 1655
- Fang, X.-P.¹ Anderson, J.E.² Chang, C.-J.³ Fanwick, P.E.⁴ McLaughlin, J.L.⁵

7
- 0037513316
- Kongsaeree, P.; Prabpai, S.; Sriubolmas, N.; Vongvein, C.; Wiyakrutta, S. J. Nat Prod. 2003, 66, 709.
- (2003) J. Nat Prod , vol.66 , pp. 709
- Kongsaeree, P.¹ Prabpai, S.² Sriubolmas, N.³ Vongvein, C.⁴ Wiyakrutta, S.⁵

8
- 0027170511
- Antoun, M. D.; Mendoza, N. T.; Rios, Y. R.; Proctor, G. R.; Wickramaratne, D. B. M.; Pezzuto, J. M.; Kinghorn, A. D. J. Nat. Prod. 1993, 56, 1423.
- (1993) J. Nat. Prod , vol.56 , pp. 1423
- Antoun, M.D.¹ Mendoza, N.T.² Rios, Y.R.³ Proctor, G.R.⁴ Wickramaratne, D.B.M.⁵ Pezzuto, J.M.⁶ Kinghorn, A.D.⁷

9
- 4544252452
- Kamisuki, S.; Takahashi, S.; Mizushina, Y.; Sakaguchi, K.; Nakata, T.; Sugawara, F. Bioorg. Med. Chem. 2004, 12, 5355.
- (2004) Bioorg. Med. Chem , vol.12 , pp. 5355
- Kamisuki, S.¹ Takahashi, S.² Mizushina, Y.³ Sakaguchi, K.⁴ Nakata, T.⁵ Sugawara, F.⁶

10
- 7244260408
- Rinner, U.; Hudlicky, T.; Gordon, H.; Pettit, G. R. Angew. Chem. Int. Ed. 2004, 43, 5342.
- (2004) Angew. Chem. Int. Ed , vol.43 , pp. 5342
- Rinner, U.¹ Hudlicky, T.² Gordon, H.³ Pettit, G.R.⁴

11
- 33947476003
- (a) Barker, R.; Fletcher, H. G. J. J. Org. Chem. 1961, 26, 4605.
- (1961) J. Org. Chem , vol.26 , pp. 4605
- Barker, R.¹ Fletcher, H.G.J.²

12
- 0028230748
- (b) Purdy, D. F.; Zintek, L. B.; Nair, V. Nucleosides Nucleotides 1994, 13, 109.
- (1994) Nucleosides Nucleotides , vol.13 , pp. 109
- Purdy, D.F.¹ Zintek, L.B.² Nair, V.³

13
- 0016000169
- Buchanan, J. G.; Edgar, A. R.; Power, M. J. J. Chem. Soc., Perkin Trans, 1 1974, 1943.
- (1974) J. Chem. Soc., Perkin Trans, 1 , pp. 1943
- Buchanan, J.G.¹ Edgar, A.R.² Power, M.J.³

14
- 0001493681
- Zhai, D.; Zhai, W.; Williams, R. M. J. Am. Chem. Soc. 1988, 110, 2501.
- (1988) J. Am. Chem. Soc , vol.110 , pp. 2501
- Zhai, D.¹ Zhai, W.² Williams, R.M.³

15
- 0028284482
- Richter, M.; Seitz, G. Arch. Pharm. 1994, 327, 365.
- (1994) Arch. Pharm , vol.327 , pp. 365
- Richter, M.¹ Seitz, G.²

16
- 0347152635
- (a) Boger, D. L.; Coleman, R. S.; Panek, J. S.; Huber, F. X.; Sauer, J. J. Org. Chem. 1985, 50, 5377.
- (1985) J. Org. Chem , vol.50 , pp. 5377
- Boger, D.L.¹ Coleman, R.S.² Panek, J.S.³ Huber, F.X.⁴ Sauer, J.⁵

17
- 0002532612
- (b) Boger, D. L.; Panek, J. S.; Patel, M. Org. Synth. 1992, 70, 79.
- (1992) Org. Synth , vol.70 , pp. 79
- Boger, D.L.¹ Panek, J.S.² Patel, M.³

18
- 0001605417
- Boger, D. L.; Coleman, R. S.; Panek, J. S.; Yohannes, D. J. Org. Chem. 1984, 49, 4405.
- (1984) J. Org. Chem , vol.49 , pp. 4405
- Boger, D.L.¹ Coleman, R.S.² Panek, J.S.³ Yohannes, D.⁴

19
- 0346392193
- Joshi, U.; Josse, S.; Pipelier, M.; Chevallier, F.; Pradère, J.-P.; Hazard, R.; Legoupy, S.; Huet, F.; Dubreuil, D. Tetrahedron Lett. 2004, 45, 1031.
- (2004) Tetrahedron Lett , vol.45 , pp. 1031
- Joshi, U.¹ Josse, S.² Pipelier, M.³ Chevallier, F.⁴ Pradère, J.-P.⁵ Hazard, R.⁶ Legoupy, S.⁷ Huet, F.⁸ Dubreuil, D.⁹

20
- 33847402500
- Purification of 23 and 24 on silica gel is not recommended; otherwise, a mixture of cyclized and non-cyclized products could be obtained.
- Purification of 23 and 24 on silica gel is not recommended; otherwise, a mixture of cyclized and non-cyclized products could be obtained.

21
- 33847413486
- NMR Data of (4R,5S, 1′R,2′R)-3-Butyl-4-hydroxy-2- methoxycarbonyl-7-oxo-5-(1′,2′,3′-trihydroxyprop-1′-yl, 1,4,5,7-tetrahydropyrano[3,4-b]pyrrole, 4R, 26, 1H NMR (400 MHz, CD3OD, δ, 0.94 [t, 3 H, Hδ(Bu, 3J, 7.3 Hz, 1.40 [m, 2 H, H γ(Bu, 1.50-1.67 [m, 2 H, Hβ(Bu, 2.85 [m, 2 H, Hα(Bu, 3.74 (dd, 1 H, H3′a, J 3′a-3′b, 11.5 Hz, J3′a-2′, 6.6 Hz, 3.83 (dd, 1 H, H3′b, J 3′b-3′a, 11.5 Hz, J3′b-2′, 4.0 Hz, 3.87 (s, 3 H, OMe, 4.00 (m, 1 H, H2′, 4.19 dd, 1 H, H1′, J1′-5, 7.9 Hz, J 1′-2′
- 20+21.2 (c 1.65, MeOH).

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.