Selective transformation of ascomycin into 11-epi-ascomycin

Tetrahedron Letters

Volumn 45, Issue 3, 2004, Pages 549-551

  Baumann, Karl ^a   Bacher, Markus ^a   Damont, Annelaure ^a   Steck, Andrea ^a  

^a Research Institute of the Vienna   (Austria)

Author keywords

Ascomycin; Binding domain; Epimerisation; Rearrangement; Tricarbonyl

Indexed keywords

11 EPIASCOMYCIN; ASCOMYCIN; LACTAM; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DIASTEREOISOMER; DRUG BINDING; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TRANSFORMATION; ISOMERIZATION; STEREOCHEMISTRY;

EID: 0347624527     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.199     Document Type: Article

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19. 3): δ (cis/trans-major isomer/trans-minor isomer, ppm): 169.99/170.26/168.65 (C1); +/52.44/52.66 (C2); 26.79/27.53/26.72 (C3); 20.83/22.01/21.06 (C4); 23.92/24.67/24.85 (C5); 40.31/44.70/44.09 (C6); 167.10*/167.13*/164.44 (C8); 199.01/193.65/200.36 (C9); 99.10/98.93/99.80 (C10); 29.28/34.88/32.39 (C11); 28.99/++/++ (C12); 71.10/70.96/n.d. (C13); 72.91/72.91/75.10 (C14); 80.61/76.32/76.95 (C15); 36.51/32.61/32.33 (C16); 27.32*/26.81*/26. 47 (C17); 50.00/49.01/48.64 (C18); 138.85/139.26/140.39 (C19); 124.45/123.59/123.38 (C20); 55.18/54.38/55.42 (C21); 214.10/213.32/214.67 (C22) ; 44.59/44.59/43.51 (C23); 69.96/70.18/69.63 (C24); 40.16*/39.98*/ 40.77 (C25); 78.10/77.77/78.70 (C26); 131.98/132.33/131.96 (C27); 14.78/14.49/14.78 (C28); 129.31/130.95/128.83 (C29); 35.32/35.46/35.32 (C30); 35.25/35.02/34.62 (C31); 84.74*/84.57*/84.61 (C32); 73.95/73.95/73.98 (C33); 31.60/31.60/31.72 (C34); ++/++/++ (C35); 25.33/25.08/25.33 (C36); 11.97*/11.89*/12.09 (C37); +/+/+ (13-OMe); 57.50/57.81/57.57 (15-OMe); +/+/+ (32-OMe); +++/15.61/15.76 (11-Me); 21.22/20.46/19.56 (17-Me); +++/16.44/+++ (19-Me); 10.31*/10.22*/10. 38 (25-Me). (*) Opposite E/Z-assignment possible; (+) one of seven signals between 56.58 and 56.96; (++) one of the five signals at 31.14, 31.09, 30.95, 30.79 and 30.73; (+++) one of three signals at 16.17, 16.14 and 16.08.