Total synthesis of an aglycone of spiramycin

Tetrahedron Letters

Volumn 39, Issue 10, 1998, Pages 1157-1160

  Oddon, G ^a   Uguen, D ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

SPIRAMYCIN;

ARTICLE; DRUG SYNTHESIS; METHYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0032485226     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10758-4     Document Type: Article

References (10)

1. 1-a) Oddon, G.; Uguen, D. Tetrahedron Lett. 1997, 38, 4411-4414;
2. b) Breuilles, P.; Oddon, G.; Uguen, D. Tetrahedron Lett. 1997, 38, 6607-6610;
3. c) Oddon, G.; Uguen, D. Tetrahedron Lett. 1998, 39, 1153-1156. The results presented herein are taken from the thesis dissertation of Gilles Oddon (Strasbourg, 1996).
4. 2-The A-6/S-6 ratio (table) was determined by HPLC (C-18 column; 1/9 isopropanol/hexane). Column chromatography of the crude methanolysis product of the S-6/A-6 mixture was performed efficiently on silica gel (Rf values (eluant: 9/1 hexane/AcOEt; 2 elutions): α-9a: 0.56; β-10a: 0.54; β-9a: 0.42; α-10a: 0.19). Structure assignment to each individual mixed-acetal was performed unambiguously by NMR, i.a. NOE experiments (see ref. 1c).
5. 3I (1 eq. each) in THF.
6. 3 solutions; [α]D values: 21 °C.
7. 5-For previous syntheses of related aglycones, see:i) Tatsuta, K.; Amemiya, Y.; Maniwa, S.; Kinoshita, M. Tetrahedron Lett. 1980, 21, 2837-2840;
8. ii) Nicolaou, K. C.; Seitz, S. P.; Pavia, M. R. J. Am. Chem. Soc. 1981, 103, 1224-1226;
9. iii) Nakajima, N.; Uoto, K.; Yonemitsu, O.; Hata, T. Chem. Pharm. Bull. 1991, 39, 64-74;
10. iv) Keck, G. E.; Palani, S. F.; Hardy, F. M. J. Org. Chem. 1994, 59, 3113-3122.