Synthesis of the acyl side chain segment of polyoxypeptins using regioselective ring-opening of chiral 2,3-epoxy alcohol

Tetrahedron Letters

Volumn 43, Issue 51, 2002, Pages 9391-9395

  Makino, Kazuishi ^a   Suzuki, Tatsuya ^a   Awane, Shinobu ^a   Hara, Osamu ^a   Hamada, Yasumasa ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

2,3 epoxy alcohol; Cyclodepsipeptide; Polyoxypeptins; Regioselective ring opening

Indexed keywords

2,3 EPOXYALCOHOL; ALCOHOL DERIVATIVE; CYCLODEPSIPEPTIDE; PEPTIDE; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; CHIRALITY; EPOXIDATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037121606     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02324-9     Document Type: Article

References (31)

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14. For nucleophilic ring-opening of 2,3-epoxy alcohols (nonbranched at C4) at C2 center, see: (a) Tius, M. A.; Fauq, A. H. J. Org. Chem. 1983, 48, 4131-4132; (b) see: Ref. 4a; (c) Tius, M. A.; Fauq, A. H. J. Am. Chem. Soc. 1986, 108, 1035-1039; (d) Kuroda, C.; Theramongkol, P.; Engebrecht, J. R.; White, J. D. J. Org. Chem. 1986, 51, 956-958; (e) Chong, J. M.; Cry, D. R.; Mar, E. K. Tetrahedron Lett. 1987, 28, 5009-5012.
15. For nucleophilic ring-opening of 2,3-epoxy alcohols (nonbranched at C4) at C2 center, see: (a) Tius, M. A.; Fauq, A. H. J. Org. Chem. 1983, 48, 4131-4132; (b) see: Ref. 4a; (c) Tius, M. A.; Fauq, A. H. J. Am. Chem. Soc. 1986, 108, 1035-1039; (d) Kuroda, C.; Theramongkol, P.; Engebrecht, J. R.; White, J. D. J. Org. Chem. 1986, 51, 956-958; (e) Chong, J. M.; Cry, D. R.; Mar, E. K. Tetrahedron Lett. 1987, 28, 5009-5012.
16. For nucleophilic ring-opening of 2,3-epoxy alcohols (nonbranched at C4) at C2 center, see: (a) Tius, M. A.; Fauq, A. H. J. Org. Chem. 1983, 48, 4131-4132; (b) see: Ref. 4a; (c) Tius, M. A.; Fauq, A. H. J. Am. Chem. Soc. 1986, 108, 1035-1039; (d) Kuroda, C.; Theramongkol, P.; Engebrecht, J. R.; White, J. D. J. Org. Chem. 1986, 51, 956-958; (e) Chong, J. M.; Cry, D. R.; Mar, E. K. Tetrahedron Lett. 1987, 28, 5009-5012.
17. For nucleophilic ring-opening of 2,3-epoxy alcohols (nonbranched at C4) at C2 center, see: (a) Tius, M. A.; Fauq, A. H. J. Org. Chem. 1983, 48, 4131-4132; (b) see: Ref. 4a; (c) Tius, M. A.; Fauq, A. H. J. Am. Chem. Soc. 1986, 108, 1035-1039; (d) Kuroda, C.; Theramongkol, P.; Engebrecht, J. R.; White, J. D. J. Org. Chem. 1986, 51, 956-958; (e) Chong, J. M.; Cry, D. R.; Mar, E. K. Tetrahedron Lett. 1987, 28, 5009-5012.
18. For nucleophilic ring-opening of 2,3-epoxy alcohols (nonbranched at C4) at C2 center, see: (a) Tius, M. A.; Fauq, A. H. J. Org. Chem. 1983, 48, 4131-4132; (b) see: Ref. 4a; (c) Tius, M. A.; Fauq, A. H. J. Am. Chem. Soc. 1986, 108, 1035-1039; (d) Kuroda, C.; Theramongkol, P.; Engebrecht, J. R.; White, J. D. J. Org. Chem. 1986, 51, 956-958; (e) Chong, J. M.; Cry, D. R.; Mar, E. K. Tetrahedron Lett. 1987, 28, 5009-5012.
19. For nucleophilic ring-opening of 2,3-epoxy alcohols (nonbranched at C4) at C2 center, see: (a) Tius, M. A.; Fauq, A. H. J. Org. Chem. 1983, 48, 4131-4132; (b) see: Ref. 4a; (c) Tius, M. A.; Fauq, A. H. J. Am. Chem. Soc. 1986, 108, 1035-1039; (d) Kuroda, C.; Theramongkol, P.; Engebrecht, J. R.; White, J. D. J. Org. Chem. 1986, 51, 956-958; (e) Chong, J. M.; Cry, D. R.; Mar, E. K. Tetrahedron Lett. 1987, 28, 5009-5012.
20. For nucleophilic ring-opening of 2,3-epoxy alcohols (nonbranched at C4) at C2 center, see: (a) Tius, M. A.; Fauq, A. H. J. Org. Chem. 1983, 48, 4131-4132; (b) see: Ref. 4a; (c) Tius, M. A.; Fauq, A. H. J. Am. Chem. Soc. 1986, 108, 1035-1039; (d) Kuroda, C.; Theramongkol, P.; Engebrecht, J. R.; White, J. D. J. Org. Chem. 1986, 51, 956-958; (e) Chong, J. M.; Cry, D. R.; Mar, E. K. Tetrahedron Lett. 1987, 28, 5009-5012.
21. For nucleophilic ring-opening of 2,3-epoxy alcohols (branched at C4) at C2 center, see: (a) Johnson, M. R.; Nakata, T.; Kishi, Y. Tetrahedron Lett. 1979, 20, 4343-4346; (b) Nagaoka, H.; Rutsch, W.; Schmid, G.; Iio, H.; Johnson, M. R.; Kishi, Y. J. Am. Chem. Soc. 1980, 102, 7962-7965; (c) Wood, R. D.; Ganem, B. Tetrahedron Lett. 1982, 23, 707-710; (d) Nagaoka, H.; Kishi, Y. Tetrahedron 1981, 37, 3873-3888; (e) Lipshutz, B. H.; Kotsuki, H.; Lew, W. Tetrahedron Lett. 1986, 27, 4825-4828; (f) Hanamoto, T.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 6195-6198.
22. For nucleophilic ring-opening of 2,3-epoxy alcohols (branched at C4) at C2 center, see: (a) Johnson, M. R.; Nakata, T.; Kishi, Y. Tetrahedron Lett. 1979, 20, 4343-4346; (b) Nagaoka, H.; Rutsch, W.; Schmid, G.; Iio, H.; Johnson, M. R.; Kishi, Y. J. Am. Chem. Soc. 1980, 102, 7962-7965; (c) Wood, R. D.; Ganem, B. Tetrahedron Lett. 1982, 23, 707-710; (d) Nagaoka, H.; Kishi, Y. Tetrahedron 1981, 37, 3873-3888; (e) Lipshutz, B. H.; Kotsuki, H.; Lew, W. Tetrahedron Lett. 1986, 27, 4825-4828; (f) Hanamoto, T.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 6195-6198.
23. For nucleophilic ring-opening of 2,3-epoxy alcohols (branched at C4) at C2 center, see: (a) Johnson, M. R.; Nakata, T.; Kishi, Y. Tetrahedron Lett. 1979, 20, 4343-4346; (b) Nagaoka, H.; Rutsch, W.; Schmid, G.; Iio, H.; Johnson, M. R.; Kishi, Y. J. Am. Chem. Soc. 1980, 102, 7962-7965; (c) Wood, R. D.; Ganem, B. Tetrahedron Lett. 1982, 23, 707-710; (d) Nagaoka, H.; Kishi, Y. Tetrahedron 1981, 37, 3873-3888; (e) Lipshutz, B. H.; Kotsuki, H.; Lew, W. Tetrahedron Lett. 1986, 27, 4825-4828; (f) Hanamoto, T.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 6195-6198.
24. For nucleophilic ring-opening of 2,3-epoxy alcohols (branched at C4) at C2 center, see: (a) Johnson, M. R.; Nakata, T.; Kishi, Y. Tetrahedron Lett. 1979, 20, 4343-4346; (b) Nagaoka, H.; Rutsch, W.; Schmid, G.; Iio, H.; Johnson, M. R.; Kishi, Y. J. Am. Chem. Soc. 1980, 102, 7962-7965; (c) Wood, R. D.; Ganem, B. Tetrahedron Lett. 1982, 23, 707-710; (d) Nagaoka, H.; Kishi, Y. Tetrahedron 1981, 37, 3873-3888; (e) Lipshutz, B. H.; Kotsuki, H.; Lew, W. Tetrahedron Lett. 1986, 27, 4825-4828; (f) Hanamoto, T.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 6195-6198.
25. For nucleophilic ring-opening of 2,3-epoxy alcohols (branched at C4) at C2 center, see: (a) Johnson, M. R.; Nakata, T.; Kishi, Y. Tetrahedron Lett. 1979, 20, 4343-4346; (b) Nagaoka, H.; Rutsch, W.; Schmid, G.; Iio, H.; Johnson, M. R.; Kishi, Y. J. Am. Chem. Soc. 1980, 102, 7962-7965; (c) Wood, R. D.; Ganem, B. Tetrahedron Lett. 1982, 23, 707-710; (d) Nagaoka, H.; Kishi, Y. Tetrahedron 1981, 37, 3873-3888; (e) Lipshutz, B. H.; Kotsuki, H.; Lew, W. Tetrahedron Lett. 1986, 27, 4825-4828; (f) Hanamoto, T.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 6195-6198.
26. For nucleophilic ring-opening of 2,3-epoxy alcohols (branched at C4) at C2 center, see: (a) Johnson, M. R.; Nakata, T.; Kishi, Y. Tetrahedron Lett. 1979, 20, 4343-4346; (b) Nagaoka, H.; Rutsch, W.; Schmid, G.; Iio, H.; Johnson, M. R.; Kishi, Y. J. Am. Chem. Soc. 1980, 102, 7962-7965; (c) Wood, R. D.; Ganem, B. Tetrahedron Lett. 1982, 23, 707-710; (d) Nagaoka, H.; Kishi, Y. Tetrahedron 1981, 37, 3873-3888; (e) Lipshutz, B. H.; Kotsuki, H.; Lew, W. Tetrahedron Lett. 1986, 27, 4825-4828; (f) Hanamoto, T.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 6195-6198.
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31. 5: C, 69.81; H, 9.05. Found: C, 69.88; H, 8.73%.