Determination of the stereoisomer of korormicin from eight possible stereoisomers by total synthesis

Tetrahedron Letters

Volumn 41, Issue 9, 2000, Pages 1465-1468

  Kobayashi, Yuichi ^a   Nakayama, Yuji ^a   Yoshida, Shinya ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Alkenyl halides; Asymmetric synthesis; Boron; Boron compounds; Korormicin; Nickel; Nickel compounds

Indexed keywords

ANTIBIOTIC AGENT; KORORMICIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034716542     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02319-9     Document Type: Article

References (25)

1. (a) Yoshikawa, K.; Takadera, T.; Adachi, K.; Nishijima, M.; Sano, H. J. Antibiot. 1997, 50, 949-953.
2. (b) Yoshikawa, K.; Nakayama, Y.; Hayashi, M.; Unemoto, T.; Mochida, K. J. Antibiot. 1999, 52, 182-185.
3. Kobayashi, Y.; Nakayama, Y.; Mizojiri, R. Tetrahedron 1998, 54, 1053-1062.
4. Kitano, Y.; Okamoto, S.; Sato, F. Chem. Lett. 1989, 2163-2164.
5. (a) Boden, E. P.; Keck, G. E. J. Org. Chem. 1985, 50, 2394-2395.
6. (b) Sunazuka, T.; Hirose, T.; Harigaya, Y.; Takamatsu, S.; Hayashi, M.; Komiyama, K.; Omura, S.; Sprengeler, P. A.; Smith III, A. B. J. Am. Chem. Soc. 1997, 119, 10 247-10 248.
7. 13C NMR spectrum of 7 were also insufficiently separated (Δδ <0.2 ppm).
8. Only one spot was seen on TLC.
9. (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
10. (b) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768-2771.
11. (c) Keinan, E.; Sinha, S. C.; Sinha-Bagchi, A; Wang, Z.-M.; Zhang, X.-L.; Sharpless, K. B. Tetrahedron Lett. 1992, 33, 6411-6414.
12. (d) Vanhessche, K. P. M.; Wang, Z.-M.; Sharpless, K. B. Tetrahedron Lett. 1994, 35, 3469-3472.
13. D) of the other four diastereomers with (R) chirality at C(5) should have, in principle, the reverse rotations of those chosen for the preparation, respectively.
14. Ho, N.-h.; le Noble, W. J. J. Org. Chem. 1989, 54, 2018-2021.
15. 1H NMR spectroscopy of the corresponding MTPA ester.
16. (a) Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 1574-1585.
17. (b) Iacono, S.; Rasmussen, J. R. In Org. Synth.; Freeman, J. P., Ed.; John Wiley: New York, 1990; Coll. Vol. 7, pp. 139-141.
18. Kraatz, U.; Hasenbrink, W.; Wamhoff, H.; Korte, F. Chem. Ber. 1971, 104, 2458-2466.
19. Supporting information of: Marshall, J. A.; Jiang, H. J. Org. Chem. 1999, 64, 971-975.
20. Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1983, 24, 391-394.
21. Kamabuchi, A.; Moriya, T.; Miyaura, N.; Suzuki, A. Synth. Commun. 1993, 23, 2851-2859.
22. 3) δ 169.9, 169.3, 133.8, 132.3, 131.3, 129.0, 126.9, 124.9, 88.3, 66.6, 57.1, 55.9, 45.9, 32.0, 31.8, 31.5, 29.51, 29.50, 29.2, 27.7, 26.6, 25.7, 24.4, 22.6, 18.0, 14.1, 8.1, -4.4, -5.2.
23. The difference is ca. one degree in each case and hence it is not necessary to consider equivocal separation of the minor diastereomer by chromatography during the synthesis.
24. Our result was presented at the Annual Meeting of the Chemical Society of Japan, March 31, 1999 (4A2 10 and 4A2 11).
25. Determination of the absolute stereochemistry of 1 by using the degradation products and a synthesis of natural 1 were presented at the same meeting: Uehara, H.; Oishi, T.; Hirama, M.; Yoshikawa, K.; Mochida, K. Presented at the Annual Meeting of the Chemical Society of Japan, March 31, 1999 (4A2 09).