Novel fragmentation reactions of Bafilomycin A1

Tetrahedron Letters

Volumn 38, Issue 39, 1997, Pages 6949-6952

  Gatti, Pier Andrea ^a   Gagliardi, Stefania ^a   Cerri, Alberto ^a   Farina, Carlo ^a  

^a SmithKline Beecham SpA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BAFILOMYCIN; BAFILOMYCIN A1;

ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030879467     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01629-8     Document Type: Article

References (11)

1. Werner, G.; Hagenmajer, H.; Drautz, H.; Baumgartner, A.; Zahner, H.; J. Antibiot. 1984, 37, 110-117.
2. Bindeseil, K.U.; Zeeck, A.; Liebigs Ann. Chem., 1994, 305-312.
3. Gatti, P.A.; Gagliardi, S.; Cerri, A.; Visconti, M.; Farina, C.; J. Org. Chem. 1996, 61, 7185-7188.
4. Gagliardi, S.; Gatti, P.A.; Cerri, A.; Farina, C.; Tetrahedron Lett. 1997, 38, 479-482.
5. Hanessian, S.; Tehim A.; Meng Q.; Granberg K.; Tetrahedron Lett. 1996, 37, 9001-9004.
6. MS conditions: ESI POS; TSQ 700; solvent: methanol/spray 4.5 kV/skimmen 60 V/capillary 220°C
7. 3): 6.65 (s, 1H, H-3); 6.5 (dd, J= 14, 11 Hz, 1H, H-12); 5.82 (dd, J= 11, 1 Hz, 1H, H-11); 5.77 (dd, J= 8, 1 Hz, 1H, H-5); 5.63-5.45 (m, 2H, H-21 and H-22); 5.18 (dd, J= 14, 8 Hz, 1H, H-13); 5.04 (dd, J= 8, 2 Hz, 1H, H-15); 3.84 (dd, J= 8, 8 Hz, 1H, H-14); 3.74 (ddd, J= 9. 3, 1 Hz, 1H, H-17); 3.72 (d, J= 1 Hz, 1H, 17-OH); 3.69 (s, 3H, 2-OMe); 3.32 (m, 1H, H-7); 3.30-3.19 (m, 2H, H-20); 3.24 (s, 3H, 14-OMe); 2.73 (dq, J= 3, 7 Hz, 1H, H-18); 2.55 (ddq, J= 8, 2, 7 Hz, 1H, H-6); 2.14 (dd, J= 14, 1 Hz, 1H, H-9ax); 2.05 (dd, J= 14, 8, 1H, H-9eq); 2.00-1.86 (m, 2H, H-8 and H-16); 1.99 (d, J= 1 Hz, 3H, 10-Me); 1.92 (d, J= 1 Hz, 3H, 4-Me); 1.70 (d, J= 4 Hz, 3H, 22-Me); 1.18 (d, J= 7 Hz, 3H, 18-Me); 1.08 (d, J= 7 Hz, 3H, 6-Me); 0.95 (d, J= 7 Hz, 3H, 8-Me); 0.91 (d, J= 7 Hz, 3H, 16-Me).
8. Everett, J.R.; J. Chem. Soc. Chem. Commun., 1987, 1878-1880.
9. 4OAc pH = 6.5, B= MeOH; linear gradient: 70-75% of B in 40 min.; flow rate 24 mL/min.
10. MS conditions: FAB NEG; matrix diethanolamine; FAB gas Xe; 8 kV; source 50° C
11. 3): 6.47 (dd, J= 15, 11 Hz, 1H, H-12); 6.44 (s, 1H, H-3); 5.83 (dd, J= 11, 1 Hz, 1H, H-11); 5.23 (dd, J= 15, 9 Hz, 1H, H-13); 5.22 (dd, J= 10, 1 Hz, 1H, H-5); 5.04 (d, J= 9 Hz, 1H, H-15); 3.84 (dd, J= 9, 9 Hz, 1H, H-14); 3.80-3.55 (m, 2H, H-17, 17-OH); 3.69 (s, 3H, 2-OMe); 3.41 (dq, J= 10, 7 Hz, 1H, H-6); 3.24 (s, 3H, 14-OMe); 2.85-2,73 (m, 1H, H-8); 2.73-2.62 (m, 1H, H-18); 2.30 (dd, J= 12, 12 Hz,1H, H-9ax); 2.20-2.08 (m, 1H, H-16); 2.13 (dd, J= 12, 3, 1H, H-9eq); 2.08 (d, J= 1 Hz, 3H, 4-Me); 1.73 (d, J= 1 Hz, 3H, 10-Me); 1.21 (d, J= 7 Hz, 3H, 18-Me); 1.09 (d, J= 7 Hz, 3H, 6-Me); 1.02 (d, J= 7 Hz, 3H, 8-Me); 0.88 (d, J= 7 Hz, 3H, 16-Me).