Enantioselective Synthesis of Aurilide, a Cytotoxic 26-Membered Cyclodepsipeptide of Marine Origin

Synlett

Volumn 1997, Issue 2, 1997, Pages 199-201

  Mutou, Tsuyoshi ^a   Suenaga, Kiyotake ^a   Fujita, Tatsuya ^a   Itoh, Takashi ^a   Takada, Noboru ^a   Hayamizu, Kozue ^a   Kigoshi, Hideo ^a   Yamada, Kiyoyuki ^a  

^a NAGOYA UNIVERSITY   (Japan)

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[No Author keywords available]

Indexed keywords

EID: 0002599179     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-753     Document Type: Article

References (19)

1. Suenaga, K.; Mutou, T.; Shibata, T.; Itoh, T.; Kigoshi, H.; Yamada, K. Tetrahedron Lett. 1996, 37, 6771.
2. Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747. Raimundo, B. C.; Heathcock, C. H. Synlett, 1995, 1213.
3. Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747. Raimundo, B. C.; Heathcock, C. H. Synlett, 1995, 1213.
4. The (36R,37R)-isomer of 6 was obtained as a minor product (14%).
5. 2
6. Mukaiyama, T.; Banno, K.; Narasaka, K. J. Am. Chem. Soc. 1974, 96, 7503. Paterson, I.; Smith, J. D.; Ward, R. A. Tetrahedron, 1995, 51, 9413.
7. Mukaiyama, T.; Banno, K.; Narasaka, K. J. Am. Chem. Soc. 1974, 96, 7503. Paterson, I.; Smith, J. D.; Ward, R. A. Tetrahedron, 1995, 51, 9413.
8. 12
9. Dess, D. B.; Martin, J. J. Org. Chem. 1983, 48, 4155.
10. 2Cl).
11. Sheehan, J. C.; Cruickshank, P. A.; Boshrt, G. L. J. Org. Chem. 1961, 26, 2525.
12. Tung, R. D.; Rich, D. H. J. Am. Chem. Soc. 1985, 107, 4242.
13. Attempts were made to construct 26-membered cyclodepsi-peptide structure, such as macrolactonization, based on other disconnections. However, they were not successful because of the low reactivity toward macrolactonization of a seco hydroxy acid or the instability of a seco amino acid.
14. Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945. Evans, D. A.; Rieger, D. L. Tetrahedron Lett. 1990, 31, 7099. Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511.
15. Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945. Evans, D. A.; Rieger, D. L. Tetrahedron Lett. 1990, 31, 7099. Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511.
16. Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945. Evans, D. A.; Rieger, D. L. Tetrahedron Lett. 1990, 31, 7099. Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511.
17. Yamada, S.; Kasai, Y.; Shioiri, T. Tetrahedron Lett. 1973, 1595.
18. Coste, J.; Le-Nguyen, D.; Castro, B. Tetrahedron Lett. 1990, 31, 205.
19. 3) δ 0.78 (d, J = 6.8 Hz, 2.55 Hl. 0.81 (d, J = 6.8 Hz, 0.45 H). 0.85-1.07 (m, 21 H). 1.23-1.90 (m. 6 H). 2.05 (m, 1 H). 2.32 (m, 1 H). 2.89 (d, J = 4.9 Hz, 0.15 H). 2.93 (d, J = 4.9 Hz, 0.85 H), 2.96 (s, 0.45 H). 3.10 (s. 3 H). 3.12 (s, 2.55 H), 3.93 (d, J = 17.1 Hz. 0.15 H), 3.99 (d, J = 15.6Hz, 0.85 H), 4.06 (d, J= 15.6 Hz, 0.85 H). 4.13 (dd, J = 2.0. 4.9Hz, 1 H). 4.27 (d, J= 17.1 Hz, 0.15 H), 4.62 (d, J = 11.7Hz, 1 H). 4.64 (dd. J = 4.9, 8.8 Hz, 0.85 H). 4.69 (dd, J = 4.9, 8.3 Hz, 0.15 H), 4.82 (m. 0.15 H), 4.85 (dd, J = 6.8, 8.8 Hz. 0.85 H), 4.90 (d, y= 11.7 Hz, 0.85 H), 4.92 (d. J= 11.7 Hz. 0.15 H). 5.29 (dd. y = 5.4, 9.3 Hz. 0.15 H), 5.47 (dd, J = 6.3, 8.3 Hz, 0.85 H), 6.74 (d, J = 8.8 Hz, 0.85 H), 6.82-6.89 (m, 0.3 H), 6.93 (d. J = 8.8 Hz, 0.85 H); 13C NMR (100 MHz. CDCl3) 5 11.8 (q). 12.6 (q), 17.39 [17.25] (q), 17.41 [17.7] (q), 19.0 (q), 19.5 (q). 22.0 [21.8] (q), 22.9 [23.1] (q). 24.7 [24.6] (d). 26.2 (t), 30.59 [30.65] (d). 30.74 (q). 31.1 [30.9] (d). 36.5 (q), 37.7 [37.8] (t), 38.6 (d), 51.2 [50.7] (d). 52.6 [52.4] (t). 53.7 [54.0] (d). 57.0 [57.3] (d), 73.95 [74.00] (d). 74.35 [74.40] (t). 94.4 [94.3] (s). 168.6 [168.3] (s). 170.2 [170.7] (s), 171.8 [171.6] (s), 172.3 [172.4] (s). 173.6 [173.7] (s) (the minor counter parts of doubled signals in the ratio of 5.6:1 are in brackets); MS (FAB) ml z 681 (M + Na)+; HRMS (FAB) calcd for C28H4935CI3N4NaO7 [(M + Na)+] 681.2564, found 681.2579. 4: a colorless amorphous powder; [ct]D28 -90.3 (c 1.09. CHCl,); IR (CHCl3) 31OO (br), 1685, 1645, 1460, 1290, 1250, 1105, 1055. 840 cm'1; 1H NMR (400 MHz, CDCl3) 6 -0.05 (s, 3 H). 0.02 (s, 3 H), 0.72 (d, J = 6.8 Hz, 3 H), 0.89 (s, 9 H), 0.96 (t. J = 7.3 Hz. 3 H), 1.54 (br s, 3H), 1.86 (br s, 3 H), 1.95-2.11 (m. 3 H). 2.15 (s. 3 H), 2.23-2.38 (m, 2 H), 3.67 (d, J = 9.3 Hz, 1 H), 4.16 (ddd. J = 3.4, 3.4, 8.8 Hz, I H), 4.53 (d, 7= 11.7Hz, 1 H), 4.63 (d, J= 11.7 Hz, 1 H), 5.30 (brt, y =6.8 Hz, 1 H), 7.06 (m. l H) (signals of one proton (COOH) were not observed); 13C NMR (67.8 MHz. CDCl3) 5 -5.3 (q), -4.4 (q), 10.4 (q), 10.7 (q), 12.3 (q). 13.8 (q). 14.0 (q), 18.1 (s), 20.8 (t), 25.8 (q, 3 C), 28.8 (t), 38.2 (d). 73.1 (t). 75.5 (d). 80.9 (d), 127.8 (s), 130.0 (d), 134.9 (s). 143.3 (d), 173.1 (s); MS (FAB) ml: 453 (M + Na)+; HRMS (FAB) calcd for C22H42NaO4SSi [(M + Na)+] 453.2471, found 453.2495.