Mono-osmylation of dehydroamino acid dienes: Synthesis of dehydroamino acids related to the azinomycins

Tetrahedron Letters

Volumn 37, Issue 4, 1996, Pages 447-450

  Armstrong, Robert W ^a   Tellew, John E ^a   Moran, Edmund J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 DEHYDRO AMINO ACID; AMINO ACID DERIVATIVE; ANTINEOPLASTIC ANTIBIOTIC; AZINOMYCIN A; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030052085     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02195-7     Document Type: Article

References (22)

1. Azinomycin B is identical to carzinophilin: Moran, E. J., Ph. D. Dissertation, University of California, Los Angeles, 1992; Salvati, M. E,. Ph. D. Dissertation, University of California, Los Angeles, 1992.
2. Azinomycin B is identical to carzinophilin: Moran, E. J., Ph. D. Dissertation, University of California, Los Angeles, 1992; Salvati, M. E,. Ph. D. Dissertation, University of California, Los Angeles, 1992.
3. Azinomycins: a) Nagaoka, K.; Matsumoto, M.; Oono, J.; Yokoi, K.; Ishizeki, S.; Nakashima, T. J. Antibiot. 1986, 39, 1527;
4. b) Yokoi, K.; Nagaoka, K.; Nakashima T. Chem. Pharm. Bull. 1986, 34, 4554;
5. c) Ishizeki, S.; Ohtsuka, M.; Irinoda, K.; Kukita, K.; Nagaoka, K.; Nakashima, T. J. Antibiot. 1987, 40, 60.
6. Carzinophilin: d) Hata, T.; Koga, F.; Sano, T.; Kanamori, K.; Matsumae, A.; Sugawara, R.; Shima, T.; Ito, S; Tomizawa, S. J. Antibiot., Ser. A, (Tokyo) 1954, 7, 107.
7. The absolute configuration of the C10-C13 stereocenters is uncertain.
8. For synthetic approaches to the azinomycins/carzinophilin, see: a) Hashimoto, M.; Terashima, S. Tetrahedron Lett. 1994, 50, 9409-9412;
9. b) Konda Y.; Machida T.; Sasaki T.; Takeda K; Takayanagi, H.; Harigaya, Y. Chem.. Pharm.. Bull. 1994, 42, 285-288;
10. c) Moran, E. J.; Tellew, J. E.; Zhao, Z. C.; Armstrong R. W. J. Org. Chem. 1993, 58, 7848-7859;
11. d) Coleman, R. S.; Carpenter, A. J. J. Org. Chem. 1992, 57, 5813-5815;
12. e) Shishido K.; Omodani T.; Shibuya M. J. Chem. Soc. Perkin Trans. I 1992, 57, 2053-2054;
13. f) Miller, S. C., Ph. D. Dissertation, University of Rochester, 1991.
14. Armstrong, R. W.; Moran, E. J.; Tellew, J. E. J. Org. Chem., submitted for publication.
15. a) Schmidt, U.; Lieberknecht, A.; Kazmaier, U.; Griesser, H.; Jung, G.; Metzger, J. Synthesis 1991, 49;
16. b) Schmidt, U.; Lieberknecht, A.; Wild, J. Synthesis 1988, 159.
17. Xu, D.; Crispino, G. A.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7570.
18. 10B was synthesized by LiOH hydrolysis of 10A, followed by DCC coupling with benzyl alcohol.
19. Derived from previously-described alcohol 8; see reference 4c.
20. 2 extraction) followed by silica gel chromatography gave (in order of elution) recovered 11A (96 mg, 40 %), 12 (20 mg, 23%), 13A (70 mg, 28%), and 13B (10 mg, 5%). Yield of 13A is 47% based on starting material converted.
21. Becker H.; Soler M. A.; Sharpless K. B. Tetrahedron 1995, 51, 1345-1376.
22. 3 = Cbz); see Ref. 4d.