Toward a total synthesis of an aglycone of spiramycin; preparation of a C-10/C-15 fragment

Tetrahedron Letters

Volumn 39, Issue 10, 1998, Pages 1153-1156

  Oddon, G ^a   Uguen, D ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

SPIRAMYCIN;

ARTICLE; CHEMICAL MODIFICATION; OXIDATION; PARTIAL DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0032485427     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)83164-4     Document Type: Article

References (18)

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12. 3SnH (1.3 eq.), and AIBN (0.04 eq.) were mixed in a Schlenk tube. After being perfectly degassed (freeze and thaw protocol), the mixture was heated at 90-95 °C for three hours in an argon atmosphere. Excess reagent was removed in vacuo and the residue was analysed by NMR;
13. 6c is consonant with an earlier report of the stability of related E-1-and Z-1-propenylstannane derivatives in similar conditions (Seyferth, D.; Vaughan, L. G. J. of Organomet. Chem. 1963, 1, 138-152).
14. 7-Breuilles, P.; Oddon, G.; Uguen, D. Tetrahedron Lett. 1997, 38, 6607-6610.
15. 2) to give, after elution of a forerun fraction containing the stannyl derivative 2c, the iodide 2a (386 mg). The iodide 2c was taken up in THF (5 ml) and TBAF (1 g) was added. The resulting solution was immediately concentrated in vacuo and excess KF was added. After 2 hours stirring the preceding filtration-evaporation-chromatography operations were applied to give additional 2a (44.7 mg; total yield: 62%).
16. 9-The condensation proceeded faster in DMF than in DMSO whatever the Ni(II)/Cr(II) ratio was, but, for unknown reasons, the yield in alcohol 2d did not exceed 40% by using DMF as solvent.
17. 10-Inanaga, J.; Hirata, K.; Saeki, T.; Katsuki, M., Yamaguchi, M. Bull. Chem. Soc. Jpn 1979, 52, 1989-1993.
18. 3 solutions.