Toward a total synthesis of an aglycone of spiramycine; two complementary accesses to a C-5/C-9 fragment

Tetrahedron Letters

Volumn 38, Issue 25, 1997, Pages 4411-4414

  Oddon, G ^a   Uguen, D ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

MACROLIDE; SPIRAMYCIN;

ACETYLATION; ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030913563     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00945-3     Document Type: Article

References (12)

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3. b) Nicolaou, K. C.; Seitz, S. P.; Pavia, M. R. J. Am. Chem. Soc. 1981, 103, 1224-1226;
4. Nakajima, N.; Uoto, K.; Yonemitsu, O.; Hata, T. Chem. Pharm. Bull. 1991, 39, 64-74; Keck, G. E.; Palani, S. F.; Hardy, F. M. J. Org. Chem. 1994, 59, 3113-3122.
5. Nakajima, N.; Uoto, K.; Yonemitsu, O.; Hata, T. Chem. Pharm. Bull. 1991, 39, 64-74; Keck, G. E.; Palani, S. F.; Hardy, F. M. J. Org. Chem. 1994, 59, 3113-3122.
6. a) Breuilles, P.; Schmittberger, T.; Uguen, D. Tetrahedron Lett. 1993, 34, 4205-4208;
7. b) Oddon, G.; Uguen, D. preceding letter.
8. 2)). The oxidation of 6a into the sulfate 6b was performed by using a protocol described by Sharpless (Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538-7539).
9. 3 solutions. [α]D values have been measured at 21°C.
10. Schmittberger, T.; Uguen, D. Tetrahedron Lett. 1995, 36, 7445-7448.
11. Eliel, E. L.; Wilken, P. H.; Fang, F. T. J. Org. Chem. 1957, 22, 231-234.
12. As determined by HPLC, by using a Pirkle column (isopropanol/hexane).