Carbohydrates in Organic Synthesis. Synthesis of 16-Membered-Ring Macrolide Antibiotics. 5. Total Synthesis of O-Mycinosyltylonolide: Synthesis of Key Intermediates

Journal of the American Chemical Society

Volumn 104, Issue 7, 1982, Pages 2027-2029

  Nicolaou, K C ^a   Pavia, M R ^a   Seitz, S P ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG ANALYSIS; DRUG IDENTIFICATION; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; O MYCINOSYLTYLONOLIDE; PRELIMINARY COMMUNICATION; THEORETICAL STUDY;

EID: 0019955935     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00371a043     Document Type: Article

References (22)

1. Part 3: Nicolaou, K. C.; Seitz, S. P.; Pavia, M. R. J. Am. Chem. Soc. 1981, 103, 1222.
2. Part 4: Nicolaou, K. C.; Pavia, M. R.; Seitz, S. P. J. Am. Chem. Soc. 1981, 103, 1224.
3. Isolation; Hamill, R. L.; Haney, M. E., Jr.; Stamper, M.; Wiley, P. F. Antibiot. Chemother. (Washington, D.C.) 1961, 11, 328.
4. Structure: Omura, S.; Matsubara, H.; Nakagawa, A.; Furusaki, A.; Matsumoto, T. J. Antibiot. Chemother. (Washington, D.C.) 1980, 33, 915.
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6. For some recent reviews on this concept see: Hanessian, S.; Dixit, D. M.; Liak, T. J. Pure Appl. Chem. 1981, 53, 129.
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11. The strategy for the construction of the 16-membered-ring macrolide antibiotics from α-d-glucose was announced by us in 1979: Nicolaou, K. C.; Pavia, M. R.; Seitz, S. P. Tetrahedron Lett. 1979, 2327.
12. Similar strategies were reported by Ziegler: Ziegler, F. E.; Gilligan, P. J.; Chakraborty, U. R. Tetrahedron Lett. 1979, 3371.
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