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Volumn , Issue 4, 2007, Pages 571-574

Asymmetric synthesis of the diene unit of methyl sartortuoate via a temperature-sensitive intramolecular Horner-Wadsworth-Emmons (HWE) reaction

(5) Yao, Hequan a Gao, Yuan a Liu, Peng a Sun, Bingfeng a Xu, Xingxiang a

a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY (China)

Author keywords

Asymmetric synthesis; Diene unit; HWE reaction; Methyl sartortuoate; Payne rearrangement

Indexed keywords

2,3 EPOXY ALCOHOL; ALCOHOL DERIVATIVE; ALKADIENE; CEMBRANOID; MEETHYL ISOSARTORTUOATE; METHYL SARCOATE; METHYL SARCOPHYTOATE; METHYL SARTORTUOATE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; DIELS ALDER REACTION; HORNER WADSWORTH EMMONS REACTION; HYDROLYSIS; REACTION ANALYSIS; TEMPERATURE SENSITIVITY;

EID: 33947274308 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-967970 Document Type: Article

Times cited : (8)

References (40)

1
- 0000930321
- (a) Su, J.; Long, K.; Peng, T.; Zheng, Q.; Lin, X. Acta Chim. Sin. 1985, 43, 796.
- (1985) Acta Chim. Sin , vol.43 , pp. 796
- Su, J.¹ Long, K.² Peng, T.³ Zheng, Q.⁴ Lin, X.⁵

2
- 0012122305
- Engl. Ed
- (b) Su, J.; Long, K.; Peng, T.; Zeng, L.; Zheng, Q.; Lin, X. Sci. Sin., Ser. B (Engl. Ed.) 1988, 31, 1172.
- (1988) Sci. Sin., Ser. B , vol.31 , pp. 1172
- Su, J.¹ Long, K.² Peng, T.³ Zeng, L.⁴ Zheng, Q.⁵ Lin, X.⁶

3
- 0011391872
- (c) Su, J.; Long, K.; Peng, T.; He, C. H.; Clardy, J. J. Am. Chem. Soc. 1986, 108, 177.
- (1986) J. Am. Chem. Soc , vol.108 , pp. 177
- Su, J.¹ Long, K.² Peng, T.³ He, C.H.⁴ Clardy, J.⁵

4
- 0000792801
- For other related compounds, see: a
- For other related compounds, see: (a) Kusumi, T.; Igari, M.; Ishitsuka, M. O.; Itezono, Y.; Nakayama, N.; Kakisawa, H. J. Org. Chem. 1990, 55, 6286.
- (1990) J. Org. Chem , vol.55 , pp. 6286
- Kusumi, T.¹ Igari, M.² Ishitsuka, M.O.³ Itezono, Y.⁴ Nakayama, N.⁵ Kakisawa, H.⁶

5
- 0027287456
- (b) Leone, P. A.; Bowden, B. F.; Carrol, A. R.; Coll, J. C.; Meehan, G. V. J. Nat. Prod. 1993, 56, 521.
- (1993) J. Nat. Prod , vol.56 , pp. 521
- Leone, P.A.¹ Bowden, B.F.² Carrol, A.R.³ Coll, J.C.⁴ Meehan, G.V.⁵

6
- 10044258428
- (c) Zeng, L.; Lan, W.; Su, J.; Zhang, G.; Feng, X.; Liang, Y.; Yang, X. J. Nat. Prod. 2004, 67, 1915.
- (2004) J. Nat. Prod , vol.67 , pp. 1915
- Zeng, L.¹ Lan, W.² Su, J.³ Zhang, G.⁴ Feng, X.⁵ Liang, Y.⁶ Yang, X.⁷

7
- 4344617216
- (d) Feller, M.; Rudi, A.; Berer, N.; Goldberg, I.; Stein, Z.; Benayahu, Y.; Schleyer, M.; Kashman, Y. J. Nat. Prod. 2004, 67, 1303.
- (2004) J. Nat. Prod , vol.67 , pp. 1303
- Feller, M.¹ Rudi, A.² Berer, N.³ Goldberg, I.⁴ Stein, Z.⁵ Benayahu, Y.⁶ Schleyer, M.⁷ Kashman, Y.⁸

8
- 0025846940
- (e) Ishitsuka, M. O.; Kusumi, T.; Kakisawa, H. Tetrahedron Lett. 1991, 32, 2917.
- (1991) Tetrahedron Lett , vol.32 , pp. 2917
- Ishitsuka, M.O.¹ Kusumi, T.² Kakisawa, H.³

9
- 0009531605
- For synthetic studies on biscembranoids by the Nakata's group, see: a
- For synthetic studies on biscembranoids by the Nakata's group, see: (a) Yasuda, M.; Ide, M.; Matsumoto, Y.; Nakata, M. Synlett 1997, 899.
- (1997) Synlett , pp. 899
- Yasuda, M.¹ Ide, M.² Matsumoto, Y.³ Nakata, M.⁴

10
- 0000698904
- (b) Yasuda, M.; Ide, M.; Matsumoto, Y.; Nakata, M. Bull. Chem. Soc. Jpn. 1998, 71, 1417.
- (1998) Bull. Chem. Soc. Jpn , vol.71 , pp. 1417
- Yasuda, M.¹ Ide, M.² Matsumoto, Y.³ Nakata, M.⁴

11
- 13244299174
- (c) Ichige, T.; Kamimura, S.; Mayumi, K.; Sakamoto, Y.; Terashita, S.; Ohteki, E.; Kanoh, N.; Nakata, M. Tetrahedron Lett. 2005, 46, 1263.
- (2005) Tetrahedron Lett , vol.46 , pp. 1263
- Ichige, T.¹ Kamimura, S.² Mayumi, K.³ Sakamoto, Y.⁴ Terashita, S.⁵ Ohteki, E.⁶ Kanoh, N.⁷ Nakata, M.⁸

12
- 0012158712
- (a) Chen, X.; Fan, C.; Xu, X. Chin. J. Chem. 2000, 18, 717.
- (2000) Chin. J. Chem , vol.18 , pp. 717
- Chen, X.¹ Fan, C.² Xu, X.³

13
- 0037433967
- (b) Hong, Z.; Chen, X.; Xu, X. Tetrahedron Lett. 2003, 44, 485.
- (2003) Tetrahedron Lett , vol.44 , pp. 485
- Hong, Z.¹ Chen, X.² Xu, X.³

14
- 0037433968
- (c) Hong, Z.; Chen, X.; Xu, X. Tetrahedron Lett. 2003, 44, 489.
- (2003) Tetrahedron Lett , vol.44 , pp. 489
- Hong, Z.¹ Chen, X.² Xu, X.³

15
- 0034659918
- (d) Gao, Y.; Nan, F.; Xu, X. Tetrahedron Lett. 2000, 41, 4811.
- (2000) Tetrahedron Lett , vol.41 , pp. 4811
- Gao, Y.¹ Nan, F.² Xu, X.³

16
- 0034640987
- (e) Liao, X.; Xu, X. Tetrahedron Lett. 2000, 41, 4641.
- (2000) Tetrahedron Lett , vol.41 , pp. 4641
- Liao, X.¹ Xu, X.²

17
- 2942591446
- (f) Liu, P.; Liao, X.; Xu, X. Chin. J. Chem. 2003, 21, 811.
- (2003) Chin. J. Chem , vol.21 , pp. 811
- Liu, P.¹ Liao, X.² Xu, X.³

18
- 2942597959
- (g) Liu, P.; Xu, X. Tetrahedron Lett. 2004, 45, 5163.
- (2004) Tetrahedron Lett , vol.45 , pp. 5163
- Liu, P.¹ Xu, X.²

19
- 33644528891
- (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
- (1983) J. Org. Chem , vol.48 , pp. 4155
- Dess, D.B.¹ Martin, J.C.²

20
- 3042741556
- (b) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
- (1991) J. Am. Chem. Soc , vol.113 , pp. 7277
- Dess, D.B.¹ Martin, J.C.²

21
- 0001848341
- (a) Marynoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
- (1989) Chem. Rev , vol.89 , pp. 863
- Marynoff, B.E.¹ Reitz, A.B.²

22
- 0018252891
- (b) Burri, K. F.; Cardone, R. A.; Chen, W. Y.; Rosen, P. J. Am. Chem. Soc. 1978, 100, 7069.
- (1978) J. Am. Chem. Soc , vol.100 , pp. 7069
- Burri, K.F.¹ Cardone, R.A.² Chen, W.Y.³ Rosen, P.⁴

23
- 33947221655
- (a) Paquette, L. A.; Wang, T. Z.; Philippo, C.; Wang, S. P. J. Am. Chem. Soc. 1991, 113, 7277.
- (1991) J. Am. Chem. Soc , vol.113 , pp. 7277
- Paquette, L.A.¹ Wang, T.Z.² Philippo, C.³ Wang, S.P.⁴

24
- 0000863170
- (b) Nicolaou, K. C.; Seitz, S. P.; Pavia, M. R. J. Am. Chem. Soc. 1982, 104, 2030.
- (1982) J. Am. Chem. Soc , vol.104 , pp. 2030
- Nicolaou, K.C.¹ Seitz, S.P.² Pavia, M.R.³

25
- 33645374504
- Stock, G.; Nakamura, E. J. Org. Chem. 1979, 44, 4010.
- (1979) J. Org. Chem , vol.44 , pp. 4010
- Stock, G.¹ Nakamura, E.²

26
- 0000476716
- Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Saka, T. Tetrahedron Lett. 1984, 25, 2183.
- (1984) Tetrahedron Lett , vol.25 , pp. 2183
- Blanchette, M.A.¹ Choy, W.² Davis, J.T.³ Essenfeld, A.P.⁴ Masamune, S.⁵ Roush, W.R.⁶ Saka, T.⁷

27
- 33947212999
- Compound 15: colorless oil; [α]D20 +15.8 (c, 0.50, MeOH, IR (film, 2932, 1717, 1676, 1448, 1184, 1137, 1098, 1037 cm-1. 1H NMR (300 MHz, CDCl3, δ, 10.09 (d, J, 7.8 Hz, 1 H, 6.14 (s, 1 H, 6.12 (d, J, 7.8 Hz, 1 H, 5.39 (s, 1 H, 5.22 (t, J, 7.5 Hz, 1 H, 4.77 (d, J, 7.2 Hz, 1 H, 4.72 (d, J, 7.2 Hz, 1 H, 4.22 (q, J, 7.2 Hz, 2 H, 4.08-4.11 (m, 1 H, 3.62-3.66 (m, 1 H, 3.39 (s, 3 H, 3.01 (d, J, 7.5 Hz, 2 H, 2.19 (s, 3 H, 1.40-2.10 (m, 8 H, 1.64 (s, 3 H, 1.30 (t, J, 7.2 Hz, 3 H, 1.20 (s, 3 H, 13C NMR (75 MHz, CDCl 3, δ, 191.7, 167.3, 161.6, 139.7, 137.2, 126.2, 124.4, 120.8, 90.7, 77.8, 74.8, 72.67, 60.6, 55.5, 36.0, 31.5, 30.1, 26.5, 24.6, 21.0, 16.1, 14.3, 14.2. ESI-MS: m/z, 409.1 [M, H, 431.1 [M, Na, HRMS ESI, m/z [M, Na, calcd for C 2
- 6: 431.2404; found: 431.2401.

28
- 33947254658
- Compound 8: colorless oil; [α]D20 +88.4 (c, 0.49, CHCl3, IR (film, 2979, 2934, 1707, 1448, 1380, 1222, 1145, 1097, 1037, 919 cm-1. 1H NMR (300 MHz, CDCl3, δ, 6.81 (t, J, 7.2 Hz, 1 H, 5.36 (t, J, 7.5 Hz, 1 H, 4.82 (d, J, 8.1 Hz, 1 H, 4.77 (d, J, 7.5 Hz, 1 H, 4.75 (d, J, 7.5 Hz, 1 H, 4.73 (d, J, 8.1 Hz, 1 H, 4.22 (q, J, 7.2 Hz, 2 H, 3.76-3.80 (m, 1 H, 3.69 (d, J, 5.1 Hz, 1 H, 3.38 (s, 3 H, 3.37 (s, 3 H, 2.70-3.10 (m, 4 H, 2.32-2.40 (m, 1 H, 2.00-2.10 (m, 2 H, 1.80-2.00 (m, 2 H, 1.50-1.70 (m, 3 H, 1.62 (s, 3 H, 1.32 (t, J, 7.2 Hz, 3 H, 1.25 (s, 3 H, 1.19 (s, 3 H, 13C NMR 75 MHz, CDCl3, δ, 168.0, 142.0, 139.1, 127.8, 123.2, 91.4, 90.9, 79.6, 77.4, 76.4, 75.9, 60.0, 55.6, 55.4, 39.7, 38.4, 33.9, 29.5, 27.7, 23.6, 22.7, 21.4, 15.4, 14.3. ESI-MS: m/z, 463.2 [M, Na
- 7: 463.2666; found: 463.2685.

29
- 33947285770
- The stereochemistry of the conjugated double bond is assigned from the chemical shift and the coupling constant data of the vinylic proton, and by analogy with closely related cyclizations
- The stereochemistry of the conjugated double bond is assigned from the chemical shift and the coupling constant data of the vinylic proton, and by analogy with closely related cyclizations.

30
- 18844410382
- Gao, Y.; Klunder, J. M.; Hanson, R. M.; Masamune, H.; Ko, S. Y.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
- (1987) J. Am. Chem. Soc , vol.109 , pp. 5765
- Gao, Y.¹ Klunder, J.M.² Hanson, R.M.³ Masamune, H.⁴ Ko, S.Y.⁵ Sharpless, K.B.⁶

31
- 33845378115
- (a) Caron, M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 1557.
- (1985) J. Org. Chem , vol.50 , pp. 1557
- Caron, M.¹ Sharpless, K.B.²

32
- 0000125419
- (b) Chong, J. M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 1560.
- (1985) J. Org. Chem , vol.50 , pp. 1560
- Chong, J.M.¹ Sharpless, K.B.²

33
- 0347968952
- Payne, G. B. J. Org. Chem. 1962, 27, 3819.
- (1962) J. Org. Chem , vol.27 , pp. 3819
- Payne, G.B.¹

34
- 0034725386
- Trost, B. M.; Madsen, R.; Guile, S. D.; Brown, B. J. Am. Chem. Soc. 2000, 122, 5947.
- (2000) J. Am. Chem. Soc , vol.122 , pp. 5947
- Trost, B.M.¹ Madsen, R.² Guile, S.D.³ Brown, B.⁴

35
- 33947240458
- Compound 20: white solid; mp 80-81°C; [α] D20 -234 (c, 0.40, CHCl3, IR (film, 2942, 1740, 1376, 1243, 1092, 1033 cm-1. 1H NMR (300 MHz, CDCl3, δ, 6.27 (d, J, 10.5 Hz, 1 H, 6.05 (dd, J, 8.4 Hz, 2 H, 4.22 (d, J, 7.5 Hz, 1 H, 4.83 (d, J, 7.5 Hz, 1 H, 4.71 (d, J, 7.5 Hz, 1 H, 4.65 (d, J, 12.3 Hz, 1 H, 4.37 (d, J, 12.3 Hz, 1 H, 4.92 (d, J, 7.5 Hz, 1 H, 3.97-4.01 (m, 1 H, 3.73 (d, J, 8.4 Hz, 1 H, 3.40 (s, 3 H, 3.32 (s, 3 H, 2.50-2.62 (m, 1 H, 2.15-2.33 (m, 1 H, 2.14-2.15 (m, 8 H, 2.054 (s, 3 H, 2.047 (s, 3 H, 1.74 (s, 3 H, 1.23 (s, 3 H, 1.21 (s, 3 H, 13C NMR (75 MHz, CDCl3, δ, 170.6, 170.1, 139.0, 134.6, 126.0, 118.1, 91.0, 90.8, 82.7, 79.9, 75.2, 69.0, 68.4, 65.2, 55.7, 55.2, 40.4, 39.8, 30.3, 24.6, 21.1 2 C, 21.0, 20.0, 19.9, 18.3. ESI-MS: m/z, 521.3 [M, Na
- 9: 521.2721; found: 521.2743. (b) The crystallographic data for 20 has been deposited at the Cambridge Crystallographic Data Centre with deposition no. CCDC 632316.

36
- 33947288656
- Compound 22: colorless oil; [α]D20 -254 (c, 0.10, CHCl3, IR (film, 2981, 2945, 2855, 1734, 1673, 1647, 1440, 1376, 1275, 1244, 1033, 910 cm-1. 1H NMR (300 MHz, CDCl3, δ, 6.98 (d, J, 10.2Hz, 1 H, 6.25 (d, J, 11.1 Hz, 1 H, 5.95 (d, J, 10.2 Hz, 1 H, 5.03 (d, J, 7.2 Hz, 1 H, 4.82 (d, J, 7.5 Hz, 1 H, 4.69 (d, J, 7.5 Hz, 1 H, 4.42 (d, J, 7.2 Hz, 1 H, 3.98-4.02 (m, 1 H, 3.70-3.73 (m, 1 H, 3.40 (s, 3 H, 3.33 (s, 3 H, 1.80-2.70 (m, 4 H, 2.27 (s, 3 H, 2.00 (s, 3 H, 1.40-1.80 (m, 6 H, 1.83 (s, 3 H, 1.23 (s, 3 H, 1.20 (s, 3 H, 13C NMR (75 MHz, CDCl3, δ, 190.2, 170.6, 145.2, 140.7, 131.9, 118.3, 91.1, 91.0, 82.5, 80.1, 75.2, 68.5, 68.4, 55.7, 55.3, 40.2, 39.6, 30.1, 27.5, 24.5, 21.3, 21.0, 20.1, 20.0, 18.8. ESI-MS: m/z, 491.1 [M, Na, HRMS ESl, m/z [M, Na, ca
- 8: 491.2615; found: 491.2605.

37
- 0001941698
- Lombardo, L. Org. Synth. 1987, 65, 81.
- (1987) Org. Synth , vol.65 , pp. 81
- Lombardo, L.¹

38
- 33751158544
- Takai, K.; Kakiuchi, T.; Kataoka, Y.; Utimoto, K. J. Org. Chem. 1994, 59, 2668.
- (1994) J. Org. Chem , vol.59 , pp. 2668
- Takai, K.¹ Kakiuchi, T.² Kataoka, Y.³ Utimoto, K.⁴

39
- 0000184375
- Petasis, N. A.; Bzowej, E. I. J. Am. Chem. Soc. 1990, 112, 6392.
- (1990) J. Am. Chem. Soc , vol.112 , pp. 6392
- Petasis, N.A.¹ Bzowej, E.I.²

40
- 33947198900
- Compound 5: colorless oil; [α]D20 -176 (c, 0.05, CHCl3, IR (film, 2925, 2853, 1742, 1458, 1375, 1240, 1144, 1092, 1072, 1034, 910 cm-1. 1H NMR (500 MHz, CDCl3, δ, 6.08-6.13 (m, 3 H, 4.96 (d, J, 7.4 Hz, 1 H, 4.93 (s, 1 H, 4.85 (s, 1 H, 4.84 (d, J, 7.3 Hz, 1 H, 5.03 (d, J, 7.3 Hz, 1 H, 4.39 (d, J, 7.4 Hz, 1 H, 4.03 (dd, J, 3.0 Hz, 1 H, 3.69 (d, J, 8.3 Hz, 1 H, 3.40 (s, 3 H, 3.33 (s, 3 H, 1.40-2.80 (m, 10 H, 1.98 (s, 3 H, 1.88 (s, 3 H, 1.73 (s, 3 H, 1.25 (s, 3 H, 1.21 (s, 3 H, 13C NMR (125 MHz, CDCl3, δ, 169.9, 143.5, 137.4, 121.2, 119.0, 113.9, 112.9, 91.1, 91.0, 82.7, 80.2, 75.3, 69.8, 68.3, 55.7, 55.2, 40.3, 39.8, 30.4, 29.7, 24.6, 22.8, 21.5, 21.1, 20.2, 18.4. ESI-MS: m/z, 489.4 [M, Na, HRMS ESI, m/z [M, Na, calcd for C26H42O7
- 7: 489.2828; found: 489.2823.

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