A correction of three reports on the synthesis of the epoxide fragment of the azinomycins

Tetrahedron Letters

Volumn 39, Issue 21, 1998, Pages 3433-3434

  Coleman, Robert S ^a   McKinley, Jason D ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 AZABICYCLO[3.1.0]HEXANE; AZINOMYCIN; EPOXIDE; ISOVALERIC ACID; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CYTOTOXICITY; DRUG SYNTHESIS; EPOXIDATION; STEREOCHEMISTRY;

EID: 0032555025     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00585-1     Document Type: Article

References (15)

1. Nagaoka, K.; Matsumoto, M.; Oono, J.; Yokoi, K.; Ishizeki, S.; Nakashima, T. J. Antibiot. 1986, 39, 1527.
2. Yokoi, K.; Nagaoka, K.; Nakashima, T. Chem. Pharm. Bull. 1986, 34, 4554.
3. Ishizeki, S.; Ohtsuka, M.; Irinoda, K.; Kukita, K.-I.; Nagaoka, K.; Nakashima, T. J. Antibiot. 1987, 40, 60.
4. Coleman, R. S.; Carpenter, A. J. J. Org. Chem. 1992, 57, 5813.
5. Coleman, R. S.; Carpenter, A. J. Tetrahedron 1997, 53, 16313.
6. Coleman, R. S.; Sarko, C. R.; Gittinger, J. P. Tetrahedron Lett. 1997, 38, 5917.
7. Ando, K.; Yamada, T.; Shibuya, M. Heterocycles 1989, 29, 2209.
8. Konda, Y.; Machida, T.; Sasaki, T.; Takeda, K.; Takayanagi, H.; Harigaya, Y. Chem. Pharm. Bull. 1994, 42, 285.
9. Bryant, H. J.; Dardonville, C. Y.; Hodgkinson, T. J.; Shipman, M.; Slawin, A. M. Z. Synlett 1996, 973.
10. Bryant, H. J.; Dardonville, C. Y.; Hodgkinson, T. J.; Hursthouse, M. B.; Malik, K. M. A.; Shipman, M. J. Chem. Soc., Perkin I 1998, 0000.
11. Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237.
12. Koch, P.; Nakatani, Y.; Luu, B.; Ourisson, G. Bull. Soc. Chim. Fr. 1983, II-189.
13. 20 +11.5 (EtOH, c 1.9) for material of 95% ee was made at a much higher concentration giving an apparent measured rotation of +0.2185°, and is therefore more reliable. We feel this may be the origin of the discrepancy.
14. Shibuya and co-workers also corrected their rotation of another azinomycin intermediate. See: Shishido, K.; Omodani, T.; Shibuya, M. J. Chem. Soc., Perkin 1 1992, 2053.
15. The data in the Shipman papers (references 8 and 9) are unambiguous with respect to absolute configuration since both a key intermediate and the final product were characterized by X-ray crystallography as the camphorsulfonate or phenelhylamine derivatives, respectively.