Total Synthesis of Amphotericin B. 3. The Final Stages

Journal of the American Chemical Society

Volumn 110, Issue 14, 1988, Pages 4696-4705

  Nicolaou, K C ^a   Daines, R A ^a   Ogawa, Y ^a   Chakraborty, T K ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHOTERICIN B;

DRUG SYNTHESIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE;

EID: 0023726525     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00222a030     Document Type: Article

References (15)

1. Nicolaou, K. C.; Chakraborty, T. K.; Daines, R. A.; Ogawa, Y.; Simpkins, N. S.; Furst, G. T. J. Am. Chem. Soc., previous paper in this issue.
2. Nicolaou, K. C.; Daines, R. A.; Uenishi, J.; Li, W. S.; Papahatjis, D. P.; Chakraborty, T. K. J. Am. Chem. Soc., previous paper in this issue.
3. Nicolaou, K. C.; Daines, R. A.; Chakraborty, T. K.; Ogawa, Y. J. Am. Chem. Soc., previous paper in this issue.
4. Isolation: Vandeputte, J.; Watchtel, J. L.; Stiller, E. T. Antibiot. Annu. 1956, 587. X-ray structure: Mechinski, W.; Shaffner, C. P.; Ganis, P.; Avitabile, G. Tetrahedron Lett. 1970, 3873. Ganis, P.; Avitabile, G.; Mechinski, W.; Shaffner, C. P. J. Am. Chem. Soc. 1971, 93, 4560.
5. Preliminary communication: Nicolaou, K. C.; Daines, R. A.; Chakraborty, T. K.; Ogawa, Y. J. Am. Chem. Soc. 1987, 109, 2821. Note that in this communication the structure of 31 was incorrectly assumed to be the regioisomer with groups R1 and R3 interchanged. This misassignment, however, was of no consequence in the overall total synthesis.
6. Hanessian, S.; Guinden, Y. J. Carbohydr. Res. 1980, 86, C3.
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10. For an excellent account on the use of trichloroimidate group in glycosidation reactions, see: Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212 and references cited therein.
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