SCOPUS 정보 검색 플랫폼

Volumn , Issue 16, 2008, Pages 2500-2502

An approach to benzannelated [5,6]-spiroketals

Author keywords

Diels Alder reactions; Heterocycles; Natural products; Ortho quinone methide; Spiro compounds

Indexed keywords

ACETAL; ACETIC ACID DERIVATIVE; BENZYL ACETATE; BUTYROLACTONE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIELS ALDER REACTION; ISOMERIZATION; SYNTHESIS;

EID: 54149095050 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078057 Document Type: Article

Times cited : (16)

References (22)

1
- 33745700300
- (a) Stierle, A. A.; Stierle, D. B.; Kelly, K. J. Org. Chem. 2006, 71, 5357.
- (2006) J. Org. Chem , vol.71 , pp. 5357
- Stierle, A.A.¹ Stierle, D.B.² Kelly, K.³

2
- 34547725721
- (b) Brasholz, M.; Sörgel, S.; Azap, C.; Reißig, H.-U. Eur. J. Org. Chem. 2007, 3801.
- (2007) Eur. J. Org. Chem , pp. 3801
- Brasholz, M.¹ Sörgel, S.² Azap, C.³ Reißig, H.-U.⁴

3
- 0034705013
- Ueno, T.;Takahashi, H.; Oda, M.; Mizunuma, M.; Yokoyama, A.; Goto, Y.; Mizushina, Y.; Sakaguchi, K.; Hayashi, H. Biochemistry 2000, 39, 5995.
- (2000) Biochemistry , vol.39 , pp. 5995
- Ueno, T.¹ Takahashi, H.² Oda, M.³ Mizunuma, M.⁴ Yokoyama, A.⁵ Goto, Y.⁶ Mizushina, Y.⁷ Sakaguchi, K.⁸ Hayashi, H.⁹

4
- 34248631941
- (a) Tsang, K. Y.; Brimble, M. A. Tetrahedron 2007, 63, 6015.
- (2007) Tetrahedron , vol.63 , pp. 6015
- Tsang, K.Y.¹ Brimble, M.A.²

5
- 33750311235
- (b) Sörgel, S.; Azap, C.; Reißig, H.-U. Org. Lett. 2006, 8, 4875.
- (2006) Org. Lett , vol.8 , pp. 4875
- Sörgel, S.¹ Azap, C.² Reißig, H.-U.³

6
- 33746895792
- (c) Waters, S. P.; Fennie, M. W.; Kozlowski, M. C. Org. Lett. 2006, 8, 3243.
- (2006) Org. Lett , vol.8 , pp. 3243
- Waters, S.P.¹ Fennie, M.W.² Kozlowski, M.C.³

7
- 33746881797
- (d) Waters, S. P.; Fennie, M. W.; Kozlowski, M. C. Tetrahedron Lett. 2006, 47, 5409.
- (2006) Tetrahedron Lett , vol.47 , pp. 5409
- Waters, S.P.¹ Fennie, M.W.² Kozlowski, M.C.³

8
- 0344927866
- (e) Tsang, K. Y.; Brimble, M. A.; Bremner, J. B. Org. Lett. 2003, 5, 4425.
- (2003) Org. Lett , vol.5 , pp. 4425
- Tsang, K.Y.¹ Brimble, M.A.² Bremner, J.B.³

9
- 0034699228
- (f) Capecchi, T.; de Koning, C. B.; Michael, J. P. J. Chem. Soc., Perkin Trans. 1 2000, 2681.
- (2000) J. Chem. Soc., Perkin Trans. 1 , pp. 2681
- Capecchi, T.¹ de Koning, C.B.² Michael, J.P.³

10
- 0032560710
- (g) Capecchi, T.; De Koning, C. B.; Michael, J. P. Tetrahedron Lett. 1998, 39, 5429.
- (1998) Tetrahedron Lett , vol.39 , pp. 5429
- Capecchi, T.¹ De Koning, C.B.² Michael, J.P.³

11
- 38349174497
- For a [3+2]-cycloaddition approach, see: (a) Wu, K.-L.; Wilkinson, S.; Reich, N. O.; Pettus, T. R. R. Org. Lett. 2007, 9, 5537.
- For a [3+2]-cycloaddition approach, see: (a) Wu, K.-L.; Wilkinson, S.; Reich, N. O.; Pettus, T. R. R. Org. Lett. 2007, 9, 5537.

12
- 33745725806
- (b) Lindsey, C. C.; Wu, K. L.; Pettus, T. R. R. Org. Lett. 2006, 8, 2365.
- (2006) Org. Lett , vol.8 , pp. 2365
- Lindsey, C.C.¹ Wu, K.L.² Pettus, T.R.R.³

13
- 0036642529
- For an excellent review of ortho-quinone methides, see: Van De Water, R. W.; Pettus, T. R. R. Tetrahedron 2002, 58, 5367.
- For an excellent review of ortho-quinone methides, see: Van De Water, R. W.; Pettus, T. R. R. Tetrahedron 2002, 58, 5367.

14
- 47749124210
- (a) Bray, C. D. Org. Biomol. Chem. 2008, 6, 2815.
- (2008) Org. Biomol. Chem , vol.6 , pp. 2815
- Bray, C.D.¹

15
- 45849133808
- For a closely related process, see
- (b) For a closely related process, see: Marsini, M. A.; Huang, Y.; Lindsey, C. C.; Wu, K.-L.; Pettus, T. R. R. Org. Lett. 2008, 10, 1477.
- (2008) Org. Lett , vol.10 , pp. 1477
- Marsini, M.A.¹ Huang, Y.² Lindsey, C.C.³ Wu, K.-L.⁴ Pettus, T.R.R.⁵

16
- 0000622856
- Loubinoux, B.; Miazimbakana, J.; Gerardin, P. Tetrahedron Lett. 1989, 30, 1939.
- (1989) Tetrahedron Lett , vol.30 , pp. 1939
- Loubinoux, B.¹ Miazimbakana, J.² Gerardin, P.³

17
- 27144476178
- Rodriguez, R.; Moses, J. E.; Adlington, R. M.; Baldwin, J. E. Org. Biomol. Chem. 2005, 3, 3488.
- (2005) Org. Biomol. Chem , vol.3 , pp. 3488
- Rodriguez, R.¹ Moses, J.E.² Adlington, R.M.³ Baldwin, J.E.⁴

18
- 43549111670
- (a) Zhou, G.; Zhu, J.; Xie, Z.; Li, Y. Org. Lett. 2008, 10, 721.
- (2008) Org. Lett , vol.10 , pp. 721
- Zhou, G.¹ Zhu, J.² Xie, Z.³ Li, Y.⁴

19
- 33646029700
- See also
- (b) See also: Zhou, G.; Zheng, D.; Da, S.; Xie, Z.; Li, Y. Tetrahedron Lett. 2006, 47, 3349.
- (2006) Tetrahedron Lett , vol.47 , pp. 3349
- Zhou, G.¹ Zheng, D.² Da, S.³ Xie, Z.⁴ Li, Y.⁵

20
- 54149099120
- General Procedure: 2-Hydroxybenzyl acetate (8a; 40 mg, 0.24 mmol) in γ-methylene-γ-butyrolactone (0.24 mL, 1.0 M) was heated at 100°C for 20 h. The cooled reaction mixture was purified by flash column chromatography (SiO2, 25% → 30% EtOAc in PE) to give 9a as a white solid (36 mg, 84, mp 107-108°C (lit.12 106°C, Rf 0.26 (EtOAc-PE, 3:7, IR: 2961, 2920, 1776 (C=O, 1582, 1489, 1447, 1251, 1220, 1170, 1093, 1055 cm-1. 1H NMR (400 MHz, CDCl3, δ, 7.07-7.17 (m, 2 H, 2 x ArCH, 6.93 (dt, J, 7.4, 1.1 Hz, 1 H, ArCH, 6.81 (dd, J, 8.1, 1.1 Hz, 1 H, ArCH, 3.06-3.18 (m, 1 H, 1 H of CH2, 2.91-3.04 (m, 1 H, 1 H of CH2, 2.79 (ddd, J, 16.5, 6.0, 2.5 Hz, 1 H, 1 H of CH 2, 2.64 (ddd, J, 17.6, 9.5, 2.5 Hz, 1 H, 1 H of CH 2, 2.52 ddd, J, 13.1, 9.5, 2.5 Hz, 1 H, 1 H of CH 2
- 3Na: 227.0684; found: 227.0690.

21
- 25444454835
- 2 (5 mol%), see: Weinert, E. E.; Frankenfield, K. N.; Rokita, S. E. Chem. Res. Toxicol. 2005, 18, 1364.
- 2 (5 mol%), see: Weinert, E. E.; Frankenfield, K. N.; Rokita, S. E. Chem. Res. Toxicol. 2005, 18, 1364.

22
- 34250547423
- Mixich, Z. Monatsh. Chem. 1965, 96, 220.
- (1965) Monatsh. Chem , vol.96 , pp. 220
- Mixich, Z.¹

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.