Total synthesis of an antifungal cyclic depsipeptide aureobasidin A

Tetrahedron

Volumn 52, Issue 12, 1996, Pages 4327-4346

  Kurome, Toru ^b   Inami, Kaoru ^a   Inoue, Tetsuya ^b   Ikai, Katsushige ^b   Takesako, Kazutoh ^b   Kato, Ikunoshin ^b   Shiba, Tetsuo ^a  

^a Protein Research Foundation   (Japan)

^b TAKARA SHUZO CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; AUREOBASIDIN A; DEPSIPEPTIDE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CHIRALITY; DRUG SYNTHESIS; MINIMUM INHIBITORY CONCENTRATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0029984290     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00132-9     Document Type: Article

References (21)

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3. Takesako, K.; Kuroda, H.; Inoue, T.; Haruna, F.; Yoshikawa, Y.; Kato, I.; Uchida, K.; Hiratani, T.; Yamaguchi, H. J. Antibiot. 1993, 46, 1414-1420.
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9. Bop-Cl; Diago-Meseguer, J.; Palomo-Coll, A. L.; Fernandez-Lizarbe, J. R.; Zugaza-Bilbao, A. Synthesis 1980, 547-551. Tung, R. D.; Dhaon, M. K.; Rich, D. H. J. Org. Chem. 1986, 51, 3350-3354.
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11. After achievement of the total synthesis of aureobasidin A, the coupling to prepare segment A with diisopropylcarbodiimide (DIPCI) and 1-hydroxy-7-azabenzotriazole (HOAt) was also evaluated to give an excellent yield (88.7%). The application of HOAt as an efficient peptide coupling additive has been reported in the following papers: Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397-4398.
12. Angell, Y. M.; García-Echeverría, C.; Rich, D. H. Tetrahedron Lett. 1994, 35, 5981-5984.
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14. The hydroxyl group of Boc-DL-HOMeVal-OBzl could not be protected with trichloroethoxycarbonyl (Troc) or benzyloxycarbonyl (Z), suggesting the low reactivity of this hydroxyl group. Therefore, we considered that no protection would be needed for the hydroxyl group during the elongation of peptide.
15. These diastereomeric peptides (L-L-D or L-D-D) after separation were hydrolyzed, respectively, with 6 N HCl for 19 h to give L-HOMeVal and D-HOMeVal, both of which were assigned in comparison with the authentic amino acids on Daicel Chiralpak WH.
16. The coupling reaction of Boc-L-MePhe-OH with HCl•H-L-Pro-OPac by the WSCD-HOBt method gave the product in 87% yield, accompanying the L-D isomer (the ratio of L-L and L-D isomers was 10 : 3). This racemization was due to intramolecular formation of the charged Schiff base in the Pro residue between the imino group and the carbonyl function of the Pac ester. Kuroda, H.; Kubo, S.; Chino, N.; Kimura, T.; Sakakibara, S. Int. J. Peptide Protein Res. 1992, 40, 114. The reaction with PyBroP afforded the desired product without racemization.
17. Ishida, T.; In, Y.; Fujikawa, A.; Urata, H.; Inoue, M.; Ikai, K.; Takesako, K.; Kato, I. J. Chem. Soc., Chem. Commun. 1992, 1231. Fujikawa, A.; In, Y.; Inoue, M.; Ishida, T. J. Org. Chem. 1994, 59, 570.
18. Ishida, T.; In, Y.; Fujikawa, A.; Urata, H.; Inoue, M.; Ikai, K.; Takesako, K.; Kato, I. J. Chem. Soc., Chem. Commun. 1992, 1231. Fujikawa, A.; In, Y.; Inoue, M.; Ishida, T. J. Org. Chem. 1994, 59, 570.
19. Benoiton, N. L.; Chen, F. M. F. Can. J. Chem. 1981, 59, 384. This oxazolinium-forming phenomenon was reported independently for N-MeVal and some N-methylamino acids by B. Castro et al. Frérot, E.; Jouin, P.; Coste, J.; Castro, B. Tetrahedron Lett. 1992, 33, 2815.
20. Benoiton, N. L.; Chen, F. M. F. Can. J. Chem. 1981, 59, 384. This oxazolinium-forming phenomenon was reported independently for N-MeVal and some N-methylamino acids by B. Castro et al. Frérot, E.; Jouin, P.; Coste, J.; Castro, B. Tetrahedron Lett. 1992, 33, 2815.
21. Ikai, K.; Takesako, K.; Shiomi, K.; Moriguchi, M.; Umeda, Y.; Yamamoto, J.; Kato, I.; Naganawa, H. J. Antibiot. 1991, 44, 925-933.