Intramolecular glycosylation approach toward constructing the macrocyclic structure of resin glycosides

Synlett

Volumn , Issue 18, 2009, Pages 2957-2960

  Son, Sang Hyun ^a   Yanagiya, Natsuko ^a   Furukawa, Jun Ichi ^a   Sakairi, Nobuo ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Dodecyl thioglycoside; Intramolecular glycosylation; Macrolide; Resin glycoside; Tricolorin

Indexed keywords

GLYCOSIDE; RESIN; TRICOLORIN A; TRICOLORIN F; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ESTERIFICATION; GLYCOSYLATION; HYDROGENOLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; SAPONIFICATION;

EID: 72149132281     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218272     Document Type: Article

References (26)

1. Pereda-Miranda R, Bah M, Curr. Top. Med. Chem. 2003 3 111
2. Cherigo L, Pereda-Miranda R, Fragoso-Serrano M, Jacobo-Herrera N, Kaatz G W., Gibbons S, J. Nat. Prod. 2008 71 1037
3. Barnes C C., Smalley M K., Manfredi K P., Kindscher K, Loring H, Sheeley D M., J. Nat. Prod. 2003 66 1457
4. Pereda-Miranda R, Mata R, Anaya A L., Wickramaratne D B. M., Pezzuto J M., Kinghorn A D., [nl]J. Nat. Prod. 1993 56 571
5. Leon I, Enriquez R G., Gnecco D, Villarreal M L., Cortes D A., Reynolds W F., Yu M, J. Nat. Prod. 2004 67 1552
6. (a) Fürstner A, Eur. J. Org. Chem. 2004 943
7. (b) Furukawa J, Sakairi N, Trends Glycosci. Glycotechnol. 2001 13 1
8. (a) Brito-Arias M, Pereda-Miranda R, Heathcock C H., [nl] J. Org. Chem. 2004 69 4567
9. (b) Zhu X.-M, He L.-L, Yang G.-L, Lei M, Chen S.-S, Yang J.-S, Synlett 2006 3510; and references cited therein
10. (a) Fürstner A, Müller T, J. Org. Chem. 1998 63 424
11. (b) Fürstner A, Müller T, J. Am. Chem. Soc. 1999 121 7814
12. (c) Fürstner A, Jeanjean F, Razon P, Angew. Chem. Int. Ed. 2002 41 2097
13. (d) Fürstner A, Jeanjean F, Razon P, Wirtz C, Mynott R, Chem. Eur. J. 2003 9 307
14. (e) Fürstner A, Jeanjean F, Razon P, Wirtz C, Mynott R, Chem. Eur. J. 2003 9 320
15. (a) Sakairi N, Wang L.-X, Kuzuhara H, J. Chem. Soc., Chem. Commun. 1991 289
16. (b) Sakairi N, Kuzuhara H, [nl] J. Chem. Soc., Chem. Commun. 1993 1874
17. (a) Bah M, Pereda-Miranda R, Tetrahedron 1996 52 13063
18. (b) Bah M, Pereda-Miranda R, Tetrahedron 1997 42 9007
19. (a) Hasegawa J, Hamada M, Miyamoto T, Nishide K, Kajimoto T, Uenishi J, Node M, Carbohydr. Res. 2005 340 2360
20. (b) Matsui H, Furukawa J, Awano T, Nishi N, Sakairi N, Chem. Lett. 2000 326
21. (c) Son S.-H, Tano C, Furukawa J, Furuike T, Sakairi N, Org. Biomol. Chem. 2008 6 1441
22. (d) Son S.-H, Tano C, Furuike T, Sakairi N, Tetrahedron Lett. 2008 49 5289
23. Son S.-H, Tano C, Furuike T, Sakairi N, Carbohydr. Res. 2009 344 285
24. Lönn H, Carbohydr. Res. 1985 139 115
25. Mootoo D R., Konradsson P, Udodong U, Fraser-Reid B, J. Am. Chem. Soc. 1988 110 5583
26. All new compounds had satisfactory data for elemental analysis or high resolution mass spectrum. Selected Physical Data Compound (R,S)-5: 1H NMR (300 MHz, CDCl3): d = 8.02?7.25 (m, 20 H, CHarom), 5.45 (t, 1 H, J3?,4? = 9.4 Hz, H-3?), 5.19 (t, 1 H, J2?,3? = 9.8 Hz, H-2?), 4.97?4.61 (m, 6 H, PhCH2), 4.57 (d, 1 H, J1?,2? = 10.0 Hz, H-1?), 4.25 (d, 1 H, J1,2 = 7.1 Hz, H-1), 3.61?3.48 (m, 4 H, H-2, H-3, H-5?, OCH), 3.41?3.33 (m, 2 H, H-5, H-4?), 3.20 (t, 1 H, J4,5 = 8.6 Hz, H-4), 2.69?2.63 (m, 2 H, SCH2), 2.26 (s, 1 H, OH), 2.09 (t, 2 H, J = 7.3 Hz, CH2COO), 1.57?0.85 (m, 56 H, H-6, H-6?, 22 CH2, 2 CH3). Although (R)-5 and (S)-5 were not distinguished by both 1H NMR and 13C NMR spectra, the diastereomeric ratio of almost 1:1 was deduced by careful HPTLC (Merck) analysis on silica gel using hexane?EtOAc (2:1). Compound (R)-6: [a]D +13.3 (c 1.05, CHCl3). 1H NMR (300 MHz, CDCl3): d = 7.90?7.19 (m, 20 H, CHarom), 5.41 (t, 1 H, J3?,4? = 8.6 Hz, H-3?), 5.23 (t, 1 H, J2?, 3? = 7.7 Hz, H-2?), 5.14 (d, 1 H, J1?,2? = 7.7 Hz, H-1?), 4.75?4.48 (m, 6 H, PhCH2), 4.39 (d, 1 H, J1,2 = 7.7 Hz, H-1), 3.85?3.76 (m, 2 H, H-2, OCH), 3.53?3.45 (m, 1 H, H-5?), 3.42 (t, 1 H, J4?,5? = 9.2 Hz, H-4?), 3.41 (t, 1 H, J3,4 = 8.5 Hz, H-3), 3.29?3.22 (m, 1 H, H- 5), 3.11 (t, 1 H, J4,5 = 9.1 Hz, H-4), 2.29?2.08 (m, 2 H, CH2COO), 1.67?1.21 (m, 30 H, H-6, H-6?, 12 CH2), 0.88 (t, 3 H, J = 6.7 Hz, CH2CH3). 13C NMR (75.5 MHz, CDCl3): d = 172.4, 165.4, 138.5, 138.1, 133.4, 130.2, 130.1, 129.0, 128.8, 128.4, 128.4, 128.2, 128.0, 99.6, 95.6, 86.4, 84.4, 82.9, 81.0, 76.2, 75.8, 75.6, 75.4, 74.9, 71.2, 71.1, 34.9, 34.5, 34.5, 32.6, 31.2, 29.4, 28.3, 28.0, 27.9, 26.9, 23.1, 18.5, 18.4, 14.6. HRMS?FAB: m/z calcd for C56H72O11 [M + Na]+: 943.4995; found: 943.4995. Compound (S)-6: [a]D +25.6 (c 0.20, CHCl3). 1H NMR (300 MHz, CDCl3): d = 7.92?7.17 (m, 20 H, CHarom), 5.42 (t, 1 H, J3?,4? = 8.6 Hz, H-3?), 5.23 (t, 1 H, J2?,3? = 8.3 Hz, H-2?), 5.07 (d, 1 H, J1?,2? = 7.6 Hz, H-1?), 4.75?4.46 (m, 6 H, PhCH2), 4.24 (d, 1 H, J1,2 = 7.8 Hz, H-1), 3.82 (dd, 1 H, J = 8.0 Hz, J2,3 = 9.3 Hz, H-2), 3.53?3.46 (m, 2 H, H-5?, OCH), 3.40 (t, 1 H, J4?,5? = 9.2 Hz, H-4?), 3.40 (t, 1 H, J3,4 = 8.4 Hz, H-3), 3.31?3.26 (m, 1 H, H-5), 3.11 (t, 1 H, J4,5 = 9.2 Hz, H-4), 2.19 (s, 2 H, CH2COO), 1.59?1.22 (m, 30 H, H-6, H-6?, 12 CH2), 0.89 (t, 3 H, J1,2 = 6.4 Hz, CH2CH3). 13C NMR (75.5 MHz, CDCl3): d = 172.4, 165.5, 138.5, 138.2, 133.4, 130.2, 130.1, 129.0, 128.9, 128.8, 128.4, 128.3, 128.3, 128.2, 128.0, 102.3, 99.5, 86.1, 84.1, 83.2, 82.2, 76.5, 75.8, 75.6, 75.5, 75.1, 71.5, 70.9, 35.3, 35.0, 34.6, 32.5, 31.6, 29.8, 28.4, 28.1, 27.3, 25.7, 25.4, 23.4, 23.1, 18.4, 14.6. HRMS?FAB: m/z calcd for C56H72O11 [M + Na]+: 943.4995; found: 943.4995. Compound 12: [a]D ?7.2 (c 0.76, CHCl3). 1H NMR (300 MHz, acetone-d6): d = 7.40?7.25 (m, 10 H, 2 CHarom), 5.40 (t, 1 H, J3?,4? = 8.9 Hz, H-3?), 4.97?4.57 (m, 6 H, PhCH2, Cl3CCH2), 4.82 (d, 1 H, J1?,2? = 10.0 Hz, H-1?), 4.73 (t, 1 H, J2?,3? = 9.6 Hz, H-2?), 4.22 (d, 1 H, J1,2 = 8.1 Hz, H-1), 4.03 (dd, 1 H, J = 2.2 Hz, J4,5 = 6.0 Hz, H-4), 4.00?3.96 (m, 1 H, H-3), 3.91 (dd, 1 H, J = 2.1, 6.5 Hz, H-5), 3.86?3.75 (m, 4 H, H-4?, H-5?, H-6?a, H-6?b), 3.63?3.60 (m, 1 H, CHO), 3.35 (t, 1 H, J2,3 = 7.6 Hz, H-2), 2.85?2.65 (m, 2 H, SCH2), 2.33? 2.20 (m, 2 H, CH2COO), 1.52?1.28 [m, 53 H, H-6, C(CH3)2, 22 CH2], 0.91?0.86 (m, 6 H, 2 CH3). Column chromatography of the mixture gave crude 12 contaminated with small amount of an unknown product in ca. 60% yield and a mixture of 11 its 3-O-Troc derivative. Repeated column chromatography gave pure 12 in 12% yield. Compound 13: [a]D +2.1 (c 0.33, CHCl3). 1H NMR (300 MHz, acetone-d6): d = 7.44?7.29 (m, 10 H, CHarom), 5.48 (t, 1 H, J3?,4? = 8.6 Hz, H-3?), 5.36 (d, 1 H, J1?,2? = 7.6 Hz, H-1?), 5.08?4.63 (m, 6 H, PhCH2, Cl3CCH2), 4.57 (dd, 1 H, J = 7.6 Hz, J2?,3? = 8.8 Hz, H-2?), 4.23 (d, 1 H, J1,2 = 8.4 Hz, H-1), 4.11 (dd, 1 H, J = 5.3 Hz, J4,5 = 7.0 Hz, H-4), 4.05 (dd, 1 H, J = 2.0 Hz, J3,4 = 5.3 Hz, H-3), 3.95?3.84 (m, 5 H, H-2, H-5, H-4?, H-6?a, H-6?b), 3.71?3.65 (m, 1 H, H-5?), 3.55?3.49 (m, 1 H, CHO), 2.33?2.00 (m, 2 H, CH2COO), 1.53?1.24 [m, 33 H, H-6, C(CH3)2, 12 CH2], 0.86 (t, 3 H, J = 6.8 Hz, CH2CH3). 13C NMR (75.5 MHz, acetone-d6): d = 171.8, 153.4, 139.1, 138.8, 128.6, 128.3, 128.2, 128.0, 127.7, 109.6, 101.5, 97.0, 95.3, 81.2, 80.5, 80.2, 77.0, 76.9, 75.5, 75.1, 74.7, 74.5, 73.5, 68.6, 68.3, 35.4, 35.2, 34.5, 32.1, 31.1, 30.1, 29.9, 29.6, 29.3, 29.1, 28.8, 28.6, 28.3, 28.2, 27.9, 27.4, 26.3, 25.4, 25.1, 24.2, 22.8, 16.7, 13.9. HRMS?FAB: m/z calcd for C48H67Cl3O13 [M + Na]+: 979.3545; found: 979.3542. Compound 19: [a]D ?20.5 (c 0.064, CHCl3). 1H NMR (600 MHz, acetone-d6): d = 7.41?7.20 (m, 25 H, CHarom), 5.06 (d, 1 H, J1?, 2? = 7.4 Hz, H-1?), 5.01 (s, 1 H, H-1), 5.01 (t, 1 H, J2,3 = 4.5 Hz, H-2), 5.01?4.61 (m, 10 H, PhCH2), 4.45 (t, 1 H, J3,4 = 6.3 Hz, H-3), 4.42 (d, 1 H, J1,2 = 6.4 Hz, H-1), 4.12 (dd, 1 H, J = 2.0 Hz, J4,5 = 5.7 Hz, H-4), 3.98?3.91 (m, 1 H, H-5), 3.94 (t, 1 H, J2,3 = 6.4 Hz, H-2), 3.80?3.74