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Volumn , Issue 20, 2006, Pages 3510-3512

Syntheses of the macrolide subunits of merremoside-type resin glycosides

Author keywords

Macrolactonization; Macrolide; Merremoside; Resin glycoside; Synthesis

Indexed keywords

GLYCIDOL; GLYCOSIDE; MACROLIDE; RESIN;

ARTICLE; DEBENZYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; MACROLACTONIZATION;

EID: 33846476139 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2006-956493 Document Type: Article

Times cited : (20)

References (25)

1
- 10244279191
- (a) Kitagawa, I.; Baek, N. I.; Kawashima, K.; Yokokawa, Y.; Yoshikawa, M.; Ohashi, K.; Shibuya, H. Chem. Pharm. Bull. 1996, 44, 1680.
- (1996) Chem. Pharm. Bull , vol.44 , pp. 1680
- Kitagawa, I.¹ Baek, N.I.² Kawashima, K.³ Yokokawa, Y.⁴ Yoshikawa, M.⁵ Ohashi, K.⁶ Shibuya, H.⁷

2
- 10244266345
- (b) Kitagawa, I.; Baek, N. I.; Yokokawa, Y.; Yoshikawa, M.; Ohashi, K.; Shibuya, H. Chem. Pharm. Bull. 1996, 44, 1693.
- (1996) Chem. Pharm. Bull , vol.44 , pp. 1693
- Kitagawa, I.¹ Baek, N.I.² Yokokawa, Y.³ Yoshikawa, M.⁴ Ohashi, K.⁵ Shibuya, H.⁶

3
- 0024335828
- Kitagawa, I.; Ohashi, K.; Kawanishi, H.; Shibuya, H.; Shinkai, K.; Akedo, H. Chem. Pharm. Bull. 1989, 37, 1679.
- (1989) Chem. Pharm. Bull , vol.37 , pp. 1679
- Kitagawa, I.¹ Ohashi, K.² Kawanishi, H.³ Shibuya, H.⁴ Shinkai, K.⁵ Akedo, H.⁶

4
- 0029779293
- For the syntheses of resin glycosides by macrolaconization, see: Tricolorins: (a) Larson, D. P.; Heathcock, C. H. J. Org. Chem. 1996, 61, 5208.
- For the syntheses of resin glycosides by macrolaconization, see: Tricolorins: (a) Larson, D. P.; Heathcock, C. H. J. Org. Chem. 1996, 61, 5208.

5
- 0031457540
- (b) Larson, D. P.; Heathcock, C. H. J. Org. Chem. 1997, 62, 8406.
- (1997) J. Org. Chem , vol.62 , pp. 8406
- Larson, D.P.¹ Heathcock, C.H.²

6
- 0030697087
- (c) Lu, S.-F.; O'Yang, Q.-Q.; Guo, Z.-W.; Yu, B.; Hui, Y.-Z. Angew. Chem., Int. Ed. Engl. 1997, 36, 2344.
- (1997) Angew. Chem., Int. Ed. Engl , vol.36 , pp. 2344
- Lu, S.-F.¹ O'Yang, Q.-Q.² Guo, Z.-W.³ Yu, B.⁴ Hui, Y.-Z.⁵

7
- 0031442147
- (d) Lu, S.-F.; O'Yang, Q.-Q.; Guo, Z.-W.; Yu, B.; Hui, Y.-Z. J. Org. Chem. 1997, 62, 8400.
- (1997) J. Org. Chem , vol.62 , pp. 8400
- Lu, S.-F.¹ O'Yang, Q.-Q.² Guo, Z.-W.³ Yu, B.⁴ Hui, Y.-Z.⁵

8
- 3042822274
- (e) Brito-Arias, M.; Pereda-Miranda, R.; Heathcock, C. H. J. Org. Chem. 2004, 69, 4567.
- (2004) J. Org. Chem , vol.69 , pp. 4567
- Brito-Arias, M.¹ Pereda-Miranda, R.² Heathcock, C.H.³

9
- 33748222800
- Calonyctins: (f) Jiang, Z.-H.; Geyer, A.; Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2520.
- Calonyctins: (f) Jiang, Z.-H.; Geyer, A.; Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2520.

10
- 0034728882
- (g) Furukawa, J.; Kobayashi, S.; Nomizu, M.; Nishi, N.; Sakairi, N. Tetrahedron Lett. 2000, 41, 3453.
- (2000) Tetrahedron Lett , vol.41 , pp. 3453
- Furukawa, J.¹ Kobayashi, S.² Nomizu, M.³ Nishi, N.⁴ Sakairi, N.⁵

11
- 4544309486
- For RCM method in the syntheses of resin glycosides, see a review: Fürstner, A. Eur. J. Org. Chem. 2004, 943.
- (a) For RCM method in the syntheses of resin glycosides, see a review: Fürstner, A. Eur. J. Org. Chem. 2004, 943.

12
- 0032489027
- Tricolorins: (b) Fürstner, A.; Müller, T. J. Org. Chem. 1998, 63, 424.
- Tricolorins: (b) Fürstner, A.; Müller, T. J. Org. Chem. 1998, 63, 424.

13
- 0038528214
- (c) Fürstner, A.; Müller, T. J. Am. Chem. Soc. 1999, 121, 7814.
- (1999) J. Am. Chem. Soc , vol.121 , pp. 7814
- Fürstner, A.¹ Müller, T.²

14
- 0037124686
- Woodrosins: d
- Woodrosins: (d) Fürstner, A.; Jeanjean, F.; Razon, P. Angew. Chem. Int. Ed. 2002, 41, 2097.
- (2002) Angew. Chem. Int. Ed , vol.41 , pp. 2097
- Fürstner, A.¹ Jeanjean, F.² Razon, P.³

15
- 0037415091
- (e) Fürstner, A.; Jeanjean, F.; Razon, P.; Wirtz, C.; Mynott, R. Chem. Eur. J. 2003, 9, 307.
- (2003) Chem. Eur. J , vol.9 , pp. 307
- Fürstner, A.¹ Jeanjean, F.² Razon, P.³ Wirtz, C.⁴ Mynott, R.⁵

16
- 0037415095
- (f) Fürstner, A.; Jeanjean, F.; Razon, P.; Wirtz, C.; Mynott, R. Chem. Eur. J. 2003, 9, 320.
- (2003) Chem. Eur. J , vol.9 , pp. 320
- Fürstner, A.¹ Jeanjean, F.² Razon, P.³ Wirtz, C.⁴ Mynott, R.⁵

17
- 84987255198
- Barry, J.; Kagan, H. B. Synthesis 1981, 453.
- (1981) Synthesis , pp. 453
- Barry, J.¹ Kagan, H.B.²

18
- 0023084868
- Menezra, C.; Mattes, H. J. Med. Chem. 1987, 30, 165.
- (1987) J. Med. Chem , vol.30 , pp. 165
- Menezra, C.¹ Mattes, H.²

19
- 0035998786
- Zhang, J.-J.; Kong, F.-Z. J. Carbohydr. Chem. 2002, 21, 89.
- (2002) J. Carbohydr. Chem , vol.21 , pp. 89
- Zhang, J.-J.¹ Kong, F.-Z.²

20
- 0034337745
- Mulard, L. A.; Ughetto-Monfrin, J. J. Carbohydr. Chem. 2000, 19, 503.
- (2000) J. Carbohydr. Chem , vol.19 , pp. 503
- Mulard, L.A.¹ Ughetto-Monfrin, J.²

21
- 0022636075
- Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212.
- (1986) Angew. Chem., Int. Ed. Engl , vol.25 , pp. 212
- Schmidt, R.R.¹

22
- 0005732938
- Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.
- (1989) Bull. Chem. Soc. Jpn , vol.1979 , pp. 52
- Inanaga, J.¹ Hirata, K.² Saeki, H.³ Katsuki, T.⁴ Yamaguchi, M.⁵

23
- 33847804686
- Corey, E. J.; Nicolaou, K. C. J. Am. Chem. Soc. 1974, 96, 5614.
- (1974) J. Am. Chem. Soc , vol.96 , pp. 5614
- Corey, E.J.¹ Nicolaou, K.C.²

24
- 33846539118
- Typical Procedure for Macrolactonization: Under argon, a solution of glycosidic acid 16 (150 mg, 0.22 mmol, PyS)2 (225 mg, 1.0 mmol, and Ph3P (303 mg, 1.2 mmol) in anhyd toluene (6 mL) was stirred for 6 h at r.t. The mixture was diluted with deoxygenated anhyd toluene (20 mL) and then was added dropwise by a syringe pump to refluxing anhyd toluene (280 mL) for 12 h. The solution was refluxed under argon for 7 d until the complete disappearance of 16 (judged by TLC analysis, The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatograph (PE-EtOAc, 6:1) to afford the macrolides 17 (20 mg, 11, as a colorless syrup together with 18 (75 mg, 58, as a colorless syrup. Spectral data for 17: Rf0.11 (PE-EtOAc, 6:1, α]D21 -8.09 (c, 0.68, CHCl 3, IR KBr, 3436, 3063, 2906, 1737, 1602, 1496, 1081, 1052 cm
- 10: 699.4084; found: 699.4079.

25
- 33846486143
- Spectral data for 19: Rf0.15 (PE-EtOAc, 2:1, α]D21 -19.1 (c, 0.44, CHCl3, IR (KBr, 3394, 2924, 1740, 1079, 1051 cm-1. 1H NMR (300 MHz, CDCl3, δ, 0.88 (t, J, 6.6 Hz, 3 H, 1.26 (d, J, 7.8 Hz, 3 H, 1.35 (d, J, 7.2 Hz, 3 H, 1.24-1.52 (m, 24 H, 1.31, 1.50 (s, 6 H, 2 × CH3, 2.34-2.43 (m, 2 H, 3.51 (dd, J, 8.1, 9.9 Hz, 2 H, 3.91-4.05 (m, 5 H, 4.47 (dd, J, 6.0, 6.6 Hz, 1 H, 4.97 (t, J, 7.8 Hz, 1 H, 5.00 (s, 1 H, 5.07 (s, 1 H, 13C NMR 50 MHz, CDCl3, δ, 14.0, 17.7, 22.5, 22.7, 23.6, 25.0, 25.3, 27.6, 28.2, 28.6, 28.7, 29.3, 30.0, 31.7, 32.0, 33.1, 33.4, 34.5, 63.5, 66.7, 71.0, 73.1, 74.4, 75.3, 75.9, 79.7, 80.0, 93.5, 95.3, 109.4, 173.7. HR-ESI-MS: m/z [M, Na, calcd for C31H54O 10: 609.3615; found: 609.3609
- 10: 609.3615; found: 609.3609.

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