Toward a total synthesis of an aglycone of spiramycin; installation of the hydroxy groups at C-4 and C-5: A model study

Tetrahedron Letters

Volumn 39, Issue 10, 1998, Pages 1149-1152

  Oddon, G ^a   Uguen, D ^a   De Cian, A ^a   Fischer, J ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

SPIRAMYCIN;

ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM; X RAY ANALYSIS;

EID: 0032485310     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10760-2     Document Type: Article

References (8)

1. 1-Breuilles, P.; Oddon, G.; Uguen, D. Tetrahedron Letters 1997, 38, 6607-6610.
2. 13C NMR: 20.52, 25.51, 39.09, 52.64, 53.1, 62.3, 102.74, 127.97, 129.33, 133.62, 140.13; [α]D -7 (c=2.6).
3. 3-a) Rf values (eluant: 95/5 hexane/AcOEt; 6 elutions): α-S-8a: 0.46; β-A-8a: 0.4; β-S-8a: 0.26; α-A-8a: 0.18;
4. 2.
5. 4-Cieplak, P.; Howard, A. E.; Powers, J. P.; Rychnovsky, S. D.; Kollman, P. A. J. Org. Chem. 1996, 61, 3662-3668.
6. -3. For all computations the Nonius OpenMolen Package (Fair, C.K. in MoIEN. An Interactive Intelligent System for Crystal Structure Analysis. Enraf-Nonius, Delft, The Netherlands, 1990) on a DEC Alpha 3600S computer was used.
7. 6-a) Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron, 1984, 40, 2247-2255;
8. b) Kolb, H. C.; VanNieuwenzhe, M. S.; Sharpless K. B. Chem. Reviews 1994, 94, 2483-2547.