Synthesis of the C1-C10 fragment of the macrolide antibiotic nystatin A1 from a chiral building block obtained via chemoenzymatic approach

Tetrahedron Letters

Volumn 37, Issue 14, 1996, Pages 2487-2490

  Bonini, C ^a   Giugliano, A ^a   Racioppi, R ^a   Righi, G ^b  

^a UNIVERSITY OF BASILICATA   (Italy)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

MACROLIDE; NYSTATIN;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029879824     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00300-0     Document Type: Article

References (29)

1. Bonini, C.; Racioppi, R.; Righi, G.; Viggiani, L. J. Org. Chem., 1993, 58, 802.
2. Bonini, C.; Racioppi, R.; Righi, G.; Rossi, L.; Viggiani, L. Tetrahedron : Asymmetry, 1993, 4, 793.
3. 1, see below ref. 8.
4. The overall reaction sequence from 1-benzyloxy propanediol, already described in the experimental section of ref.2, was improved in many reaction steps (which are practically nearly quantitative): a major limitation for a further improvement appears the aldol condensation of 1-benzyloxypropionaldehyde, with the dianion of methyl acetoacetate. Anyway the yield of this reaction was improved up to 48%.
5. For the total synthesis of Amphotericin B see Nicolaou, K.C.; Daines, R.A.; Ogawa, Y.; Chakraborty, T.K. J. Am. Chem. Soc. 1988, 110, 4696 and previous work therein reported. For a complete list of references on the Amphotericin B chemistry see: Furstner, A.; Baumgartner, J.; Tetrahedron , 1993, 49, 8541.
6. For the total synthesis of Amphotericin B see Nicolaou, K.C.; Daines, R.A.; Ogawa, Y.; Chakraborty, T.K. J. Am. Chem. Soc. 1988, 110, 4696 and previous work therein reported. For a complete list of references on the Amphotericin B chemistry see: Furstner, A.; Baumgartner, J.; Tetrahedron , 1993, 49, 8541.
7. a) Hazen, E.L.; Brown, P. Science, 1950, 112, 423.
8. b) Chong, C.N.; Rickards, R.W. Tetrahedron Lett. , 1970, 11, 5145.
9. c) Borowski, E.; Zielinski, J.; Falkowski, L.; Ziminskii, T.; Golik, J.; Kolodziejczyk, P.; Jereczek, E.; Gdulewicz, M.; Shenin, Y.; Kotienko, T. Tetrahedron Lett. 1971, 12, 685.
10. d) Dutcher, J.D.; Walters, D.R.; Wintersteiner, O. J. Org. Chem., 1963, 28, 995.
11. e) Von Saltza, M.; Dutcher, J.D.; Reid, J.; Wintersteiner, O. J. Org. Chem., 1963, 28, 999.
12. f) Jereczek, E.; Sowinski, P.; Zielinski, J.; Borowski, E. Inst. Nucl. Phys. Cracow. Rep. 1973, 232.
13. g) Iketa, M.; Suzuki, M.; Djerassi, C. Tetrahedron Lett. , 1987, 28, 3745.
14. Lancelin, J.M.; Beau, J.M. Tetrahedron Lett.., 1989, 30, 4521.
15. Nicolaou, K.C.; Ahn, K.H. Tetrahedron Lett.., 1989, 30, 1217.
16. Prandi, J.; Beau, J.M. Tetrahedron Lett. , 1989, 30, 4517.
17. Lancelin, J.M.; Paquet, F.; Beau, J.M. Tetrahedron Lett. , 1988, 29, 2827.
18. Bonini, C.; Righi, G.; Rossi, L. Tetrahedron , 1992, 48, 9801.
19. Brown, H.C.; Jadhav, P.K. J. Am. Chem. Soc. 1983, 105, 2092. Jadhav, P.K.; Bhat, K.S.; Perumal, T.; Brown, H.C. J. Org. Chem., 1986, 51, 432.
20. Brown, H.C.; Jadhav, P.K. J. Am. Chem. Soc. 1983, 105, 2092. Jadhav, P.K.; Bhat, K.S.; Perumal, T.; Brown, H.C. J. Org. Chem., 1986, 51, 432.
21. The need for buffered conditions was imposed by labile acid acetonide function. Other methodologies (i.e. Swem oxidation) did not give better results.
22. 2OH, the alternative methodology with 8-hydroxyquinoline was used (see Brown, H.C.; Racherta, U.S.; Liao, Y.; Khanna, V.V. J. Org. Chem., 1992, 57, 6608).
23. 1H-NMR spectroscopy.
24. 3).
25. 3).
26. 3).
27. 1H-NMR spectrum in comparison with 8. Further details will be given in a forthcoming paper.
28. All new compounds exhibited satisfactory spectroscopic exact mass data.
29. This work was partially supported by a MURST 40% grant.