Total synthesis of the antifungal cyclic depsipeptides Sch 57697 and aureobasidin A

Tetrahedron Letters

Volumn 37, Issue 32, 1996, Pages 5661-5664

  Jao, Edwin ^a   Cooper, Alan B ^a   Rane, Dinanath F ^a   Saksena, Anil K ^a   Desai, Jagdish ^a   Wang, James ^a   Girijavallabhan, Viyyoor M ^a   Ganguly, Ashit K ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; AUREOBASIDIN A; CYCLOPEPTIDE; DEPSIPEPTIDE; SCH 57697; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CANDIDA TROPICALIS; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

CANDIDA ALBICANS; CANDIDA TROPICALIS;

EID: 0030570905     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01199-9     Document Type: Article

References (27)

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2. 1 Takesako, K.; Ikai, K.; Haruna, F.; Endo, M.; Shimkanaka, K.; Sosn, E.; Nakamura, T.; Kato, I.; Yamaguchi, H. J. Antibiot., 1991, 44, 919 and Ikai, K.; Takesako, K.; Shiomi, K.; Moriguchi, M.; Umeda, Y.; Yamamoto, J.; Kato, I. Naganawa, H. J. Antibiot. 1991, 44, 925.
3. 2 a) Ikai, K.; Takesako, K.; Mizutani, S.; Yamamoto, J; Ogawa, Y.; Kato, I. J. Antibiot.,. 1991, 44, 1187;
4. b) Ikai, K.; Shiomi, K.; Takesako, K.; and Kato, I. ibid. 1991, 44, 1199.
5. 3 Kurome, T.; Inami, K.; Inoue, T.; Ikai, K.; Takesako, K.; Kato, I.; Shiba, T. Chemistry Letters. 1993, 1873; Kurome, T; Inami, K; Inoue, T; Ikai, K; Takesako, K; Kato, I; Shibe, T Tetrahedron. 1996, 52 no. 12, 4327.
6. 3 Kurome, T.; Inami, K.; Inoue, T.; Ikai, K.; Takesako, K.; Kato, I.; Shiba, T. Chemistry Letters. 1993, 1873; Kurome, T; Inami, K; Inoue, T; Ikai, K; Takesako, K; Kato, I; Shibe, T Tetrahedron. 1996, 52 no. 12, 4327.
7. 4 a) McDermott, J.R.; Benoiton, N.L. Can. J. Chem. 1973, 51, 2551, 2562.
8. b) Wenger, R.M., Helv. Chim. Acta. 1983, 66, 2672.
9. 5 Ishida, T,; In, Y.; Fujikawa, A.; Urata, H.; Inoue, M.; Ikai, K.; Takesako, K.; Kato, I.; J. Chem. Soc., Chem. Commun. 1992, 1231.
10. 6 Cheung, S.T.; Benoiton, N.L. Can J. Chem. 1977, 55, 906.
11. 7 Abbreviations: BOP: Benzotriazol-1-yloxy-tris(dimethyl-amino)phosphonium hexafluorophosphate; BOP-Cl: Bis(2-oxo-3-oxazolidinyl)phosphinic chloride; DCC: dicyclohexylcarbodiimide; DEC: 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; Boc: t-butoxycarbonyl; HMP: (2R)-hydroxy-(3R)-methylpentanoic acid; HOObt: 3-hydroxy-4-oxo-3,4-dihydro-1,2,3-benzotriazine; HOB1: 1-hydroxybenzotriazole; NMM: N-methylmorpholine; Piv-Cl: pivaloyl chloride;TBS: tert.butyldimethylsilyl; TFA: trifluoroacetic acid; OHMeVal: 3-hydroxy-N-methylvaline; MeVal-OBn: N-methylvaline-O-benzyl ester; Leu-OBn: leucine-O-benzylester
12. 8 Wenger, R. M. Angewandte Chemie. 1985, 24, 77, and references cited therein.
13. 9 The extent of racemization and the absolute stereochemistry were proven by synthesizing the correct tripeptide through an alternative coupling sequence where no racemization was observed: MeVal→MeVal-Leu→Aile-MeVal-Leu
14. 10 Vold, A.; Konig, W. US Patent. 1989, 4806641.
15. 11 Godfrey, J. D.; Mueller, R. H.; Von Langen, D. J., Tetrahedron Lett., 1986, 27, 2793.
16. 12 Su-Sun, W.; Gisin, B. F.; Winter, D. P.; Makofske, R.; Kulesha, I. D.; Tzougraki, C.; Meienhofer, J. J. Org. Chem. 1977, 1286.
17. 13 Gilon, C.; Klausner, Y. Tetrahedron Lett. 1979, 40, 3811.
18. 14 Van Der Auwera, C.; Anteiunis, M. J. O. Int. J. Peptide Protein Res. 1987, 29, 574.
19. 3)
20. 16 Castro, B; Dormoy, J.-R., Tetrahedron Lett., 1975, 3243.
21. D= -138 (c-1, EtOH)for 1b.
22. D=-51.4
23. 19 Slusarchyk, W. A.; Gougoutas, J.; Dejneka, T.; Koster, W. H.; Dronenthal, D. R.; Malley, M.; Perri, M. G.; Routh, F. L.; Sundeen, J. E.; Weaver, E. R.; Zahler, R. Tetrahedron Lett. 1986, 27, 2789. Note: D,L-N-Me-N-Boc-β-hydroxyvaline could not be resolved in this manner.
24. 20 L-Boc-hydroxymethylvaline could not be resolved under these conditions.
25. 21 The depsidipeptide was treated with 2 equivalents of silver oxide and 5 equivalents of methyl iodide in DMF at ambient temperature for 18 hours. The reaction mixture was filtered and chromatographed on silica gel.
26. D= -217.6 (c=1.0, MeOH)
27. 23 Coupling of OHMeVal containing peptides at the amine terminus of OHMeVal resulted in low yields. Aureobasidin A was also synthesized by first coupling tripeptide B with depsi tripeptide C using Piv-Cl/nmm to obtain a new hexapeptide B-C in 18% yield. This was then coupled to tripeptide A using Piv-Cl/nmm to obtain nona depsi peptide 17 in 56 % yield. These are not optimized yields.