Total synthesis of 16-membered tetraene macrolide hygrolidin

Tetrahedron Letters

Volumn 37, Issue 50, 1996, Pages 9077-9080

  Makino, Kazuishi ^a   Nakajima, Noriyuki ^a,c   Hashimoto, Shun Ichi ^a   Yonemitsu, Osamu ^b  

^a HOKKAIDO UNIVERSITY   (Japan)

^b OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

^c TOYAMA PREFECTURAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HYGROLIDIN; MACROLIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG SYNTHESIS; ESTERIFICATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030577465     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02133-8     Document Type: Article

References (26)

1. 2. Seto, H.; Akao, H.; Furihata, K.; Otake, N. Tetrahedron Lett. 1982, 23, 2667.
2. 3. Seto, H.; Tajima, I.; Akao, H.; Furihata, K.; Otake, N. J. Antibiot. 1984, 37, 610.
3. 4. Werner, G.; Hagenmaier, H.; Albert, K.; Kohlshorn, H.; Drautz, H. Tetrahedron Lett. 1983, 24, 5193.
4. 5. (a) Kinashi, H.; Someno, K.; Sakaguchi, K.; Higashijima, T.; Miyazawa, T. Tetrahedron Lett. 1981, 22, 3857, 3861.
5. (b) Westley, J. W.; Liu, C.-M.; Sello, L. H.; Evans, R. H.; Troupe, N.; Blount, J. F.; Chiu, A. M.; Todaro, L. J.; Miller, P. A. J. Antibiot. 1984, 37, 1738.
6. 6. (a) Bowman, E. J.; Siebers, A.; Altendorf, K. Proc. Natl. Acad. Sci. USA. 1988, 85, 7972.
7. (b) Dröse, S.; Bindseil, K. U.; Bowman, E. J.; Siebers, A.; Zeeck, A.; Altendorf, K. Biochemistry 1993, 32, 3902.
8. 7. Baker, G. H.; Brown, P. J.; Dorgan, R. J. J.; Everett, J. R. J. Chem. Soc. Perkin Trans. 2 1989, 1073.
9. 8. Evans, D. A.; Calter, M. A. Tetrahedron Lett. 1993, 34, 6871.
10. 9. (a) Toshima, K.; Jyojima, T.; Yamaguchi, H.; Murase, H.; Yoshida, T.; Matsumura, S.; Nakata, M. Tetrahedron Lett. 1996, 37, 1069.
11. (b) Toshima, K.; Yamaguchi, H.; Jyojima, T.; Noguchi, Y.; Nakata, M.; Matsumura, S.; Tetrahedron Lett. 1996, 37, 1073.
12. 10. Makino, K.; Kimura, K.; Nakajima, N.; Hashimoto, S.; Yonemitsu, O. Tetrahedron Lett. preceding paper.
13. 11. (a) Hikota, M.; Tone, H.; Horita, K.; Yonemitsu, O. J. Org. Chem. 1990, 55, 7.
14. (b) Yonemitsu, O. J. Synth. Org. Chem. Jpn. 1994, 52, 946.
15. (c) Matsushima, T.; Horita, K.; Nakajima, N.; Yonemitsu, O. Tetrahedron Lett. 1996, 37, 385.
16. 12. Goto, H.; Osawa, E. J. Chem. Soc. Perkin Trans. 2 1993, 187.
17. 13. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.
18. 14. Since removal of even the triethylsilyl protecting group at C7 proved to be problematic after macrolactonization, the seco-acid without protection of the C7 hydroxyl group was used. No difference in lactonization was observed whether it was protected or not.
19. 1H-NMR analysis of the crude mixture.
20. + 1329.7798, found 1329.7797.
21. 17. The reaction is presumed to proceed through the common intermediacy of the acyl pyridinium salt formed from 7 or 8 with DMAP, wherein the regenerated seco-acid 4 in the latter reaction could be used for macrolactonization in the presence of large quantities of 2,4,6-trichlorobenzoyl chloride.
22. 21 enolates of 3 and its C22 epimer 3′ (hygrolide numbering) with the chiral model aldehyde 14 were explored. As seen from the table, it is evident that both (Z)-boron and chlorotitanium enolates of 3′ exhibit an exceptionally high order of selectivity for syn aldol anti-Felkin diastereomer 15, whereas those of 3 show a modest level of π-facial selectivity. table presented
23. 19. Hamana, H.; Sasakura, K.; Sugasawa, T. Chem. Lett. 1984, 1729.
24. 20. Chow, H.-F.; Seebach, D. Helv. Chim. Acta 1986, 69, 604.
25. 21. Evans, D. A.; Urpf, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215.
26. 22. Corey, E. J.; Ponder J. W. Tetrahedron Lett. 1984, 25, 4325.