Synthesis of (+)-Antimycin A3. Use of the Oxazole Ring in Protecting and Activating Functions

Journal of the American Chemical Society

Volumn 107, Issue 5, 1985, Pages 1423-1424

  Wasserman, Harry H ^a   Gambale, Ronald J ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMYCIN A3; DRUG ANALYSIS; DRUG IDENTIFICATION; DRUG SYNTHESIS; METHODOLOGY; NONHUMAN; PRELIMINARY COMMUNICATION; PRIORITY JOURNAL; THEORETICAL STUDY;

EID: 0021923154     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00291a059     Document Type: Article

References (10)

1. (a) For isolation of antimycin A3, see: Lockwood, J. L.; Leben, C.; Keitt, G. W. Phytopathology 1954, 44, 438 and references therein. (b) For structural determination, see: Kinoshita, M.; Aburaki, S.; Umezawa, S. J. Antibiot. 1972, 25, 373 and references therein.
2. Liu, W.-C.; Strong, F. M. J. Am. Chem. Soc. 1959, 81, 4387.
3. 3in optically active form, see: Aburaki, S.; Kinoshita, M. Bull. Chem. Soc. Jpn. 1979, 52, 198 and references therein.
4. Nakata, T.; Fukui, M.; Oishi, T. Tetrahedron Lett. 1983, 24, 2657.
5. Wasserman, H. H.; Gambale, R. J.; Pulwer, M. J. Tetrahedron 1981, 37, 4059.
6. (a) Massad, S. K.; Hawkins, L. D.; Baker, D. C. J. Org. Chem. 1983, 48, 5180. (b) Kelly, T. R.; Kaul, P. N. J. Org. Chem. 1983, 48, 2775.
7. Kieczykowski, G. R.; Quesada, M. L.; Schlessinger, R. H. J. Am. Chem. Soc. 1980, 102, 782.
8. Compound 7 exhibited physical and spectroscopic properties (bp, [α]23D, IR) in complete agreement with the values reported by M. Kinoshita, 3 In addition, the 90-MHz 1H NMR spectrum was entirely consistent with a 100-MHz spectrum graciously provided by M. Kinoshita. For alternate syntheses, see: Heathcock, C. H.; Pirrung, M. C.; Lampe, J.; Buse, C. T.; Young, S. D. J. Org. Chem. 1981, 46, 2290 and references therein.
9. Yonehara, H.; Takeuchi, S. J. Antibiot., Ser. A 1958, 11, 122, 254.
10. Ziegler, F. E.; Berger, G. D. Synth. Commun. 1979, 9, 539.