Synthetic Route to the GE3 Cyclodepsipeptide

Organic Letters

Volumn 4, Issue 11, 2002, Pages 1903-1906

  Hale, Karl J ^a   Lazarides, Linos ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

A 83586C; ANTIINFECTIVE AGENT; ANTINEOPLASTIC ANTIBIOTIC; CYCLOPEPTIDE; DEPSIPEPTIDE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; GE3 COMPOUND; LACTAM; PEPTIDE;

ARTICLE; CHEMISTRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

ANTI-BACTERIAL AGENTS; ANTIBIOTICS, ANTINEOPLASTIC; DEPSIPEPTIDES; INDICATORS AND REAGENTS; LACTAMS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; PEPTIDES; PEPTIDES, CYCLIC;

EID: 0037198760     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025895u     Document Type: Article

References (24)

1. Sakai, Y.; Yoshida, T.; Tsujita, T.; Ochiai, K.; Agatsuma, T.; Saitoh, Y.; Tanaka, F.; Akiyama, T.; Akinaga, S.; Mizukami, T. J. Antibiot. 1997, 50, 659.
2. For a synthesis of the GE3 acyl side chain, see: Makino, K.; Henmi, Y.; Hamada, Y. Synlett 2002, 613.
3. For the first total synthesis of A83586C, see: (a) Hale, K. J.; Cai, J. J. Chem. Soc. Chem. Comm. 1997, 2319. (b) Hale, K. J.; Cai, J.; Delisser, V. M. Tetrahedron Lett. 1996, 37, 9345-9348. (c) Hale, K. J.; Cai, J. Tetrahedron Lett. 1996, 37, 4233-4236. (d) Hale, K. J.; Cai, J.; Manaviazar, S.; Peak, S. A. Tetrahedron Lett. 1995, 36, 6965-6968. (e) Hale, K. J.; Delisser, V. M.; Yeh, L.-K.; Peak, S. A.; Manaviazar, S.; Bhatia, G. S. Tetrahedron Lett. 1994, 35, 7685-7688. (f) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181-9188. (g) Hale, K. J.; Bhatia, G. S.; Peak, S. A.; Manaviazar, S. Tetrahedron Lett. 1993, 34, 5343-5346. (h) For a detailed account of our A83586C synthesis and the synthesis of other complex cyclodepsipeptides, see: Hale, K. J.; Bhatia, G. S.; Frigerio, M. The Chemical Synthesis of Natural Products; Hale, K. J., Ed.; Sheffield Academic Press: Sheffield, 2000; Chapter 12, p 349.
4. For the first total synthesis of A83586C, see: (a) Hale, K. J.; Cai, J. J. Chem. Soc. Chem. Comm. 1997, 2319. (b) Hale, K. J.; Cai, J.; Delisser, V. M. Tetrahedron Lett. 1996, 37, 9345-9348. (c) Hale, K. J.; Cai, J. Tetrahedron Lett. 1996, 37, 4233-4236. (d) Hale, K. J.; Cai, J.; Manaviazar, S.; Peak, S. A. Tetrahedron Lett. 1995, 36, 6965-6968. (e) Hale, K. J.; Delisser, V. M.; Yeh, L.-K.; Peak, S. A.; Manaviazar, S.; Bhatia, G. S. Tetrahedron Lett. 1994, 35, 7685-7688. (f) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181-9188. (g) Hale, K. J.; Bhatia, G. S.; Peak, S. A.; Manaviazar, S. Tetrahedron Lett. 1993, 34, 5343-5346. (h) For a detailed account of our A83586C synthesis and the synthesis of other complex cyclodepsipeptides, see: Hale, K. J.; Bhatia, G. S.; Frigerio, M. The Chemical Synthesis of Natural Products; Hale, K. J., Ed.; Sheffield Academic Press: Sheffield, 2000; Chapter 12, p 349.
5. For the first total synthesis of A83586C, see: (a) Hale, K. J.; Cai, J. J. Chem. Soc. Chem. Comm. 1997, 2319. (b) Hale, K. J.; Cai, J.; Delisser, V. M. Tetrahedron Lett. 1996, 37, 9345-9348. (c) Hale, K. J.; Cai, J. Tetrahedron Lett. 1996, 37, 4233-4236. (d) Hale, K. J.; Cai, J.; Manaviazar, S.; Peak, S. A. Tetrahedron Lett. 1995, 36, 6965-6968. (e) Hale, K. J.; Delisser, V. M.; Yeh, L.-K.; Peak, S. A.; Manaviazar, S.; Bhatia, G. S. Tetrahedron Lett. 1994, 35, 7685-7688. (f) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181-9188. (g) Hale, K. J.; Bhatia, G. S.; Peak, S. A.; Manaviazar, S. Tetrahedron Lett. 1993, 34, 5343-5346. (h) For a detailed account of our A83586C synthesis and the synthesis of other complex cyclodepsipeptides, see: Hale, K. J.; Bhatia, G. S.; Frigerio, M. The Chemical Synthesis of Natural Products; Hale, K. J., Ed.; Sheffield Academic Press: Sheffield, 2000; Chapter 12, p 349.
6. For the first total synthesis of A83586C, see: (a) Hale, K. J.; Cai, J. J. Chem. Soc. Chem. Comm. 1997, 2319. (b) Hale, K. J.; Cai, J.; Delisser, V. M. Tetrahedron Lett. 1996, 37, 9345-9348. (c) Hale, K. J.; Cai, J. Tetrahedron Lett. 1996, 37, 4233-4236. (d) Hale, K. J.; Cai, J.; Manaviazar, S.; Peak, S. A. Tetrahedron Lett. 1995, 36, 6965-6968. (e) Hale, K. J.; Delisser, V. M.; Yeh, L.-K.; Peak, S. A.; Manaviazar, S.; Bhatia, G. S. Tetrahedron Lett. 1994, 35, 7685-7688. (f) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181-9188. (g) Hale, K. J.; Bhatia, G. S.; Peak, S. A.; Manaviazar, S. Tetrahedron Lett. 1993, 34, 5343-5346. (h) For a detailed account of our A83586C synthesis and the synthesis of other complex cyclodepsipeptides, see: Hale, K. J.; Bhatia, G. S.; Frigerio, M. The Chemical Synthesis of Natural Products; Hale, K. J., Ed.; Sheffield Academic Press: Sheffield, 2000; Chapter 12, p 349.
7. For the first total synthesis of A83586C, see: (a) Hale, K. J.; Cai, J. J. Chem. Soc. Chem. Comm. 1997, 2319. (b) Hale, K. J.; Cai, J.; Delisser, V. M. Tetrahedron Lett. 1996, 37, 9345-9348. (c) Hale, K. J.; Cai, J. Tetrahedron Lett. 1996, 37, 4233-4236. (d) Hale, K. J.; Cai, J.; Manaviazar, S.; Peak, S. A. Tetrahedron Lett. 1995, 36, 6965-6968. (e) Hale, K. J.; Delisser, V. M.; Yeh, L.-K.; Peak, S. A.; Manaviazar, S.; Bhatia, G. S. Tetrahedron Lett. 1994, 35, 7685-7688. (f) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181-9188. (g) Hale, K. J.; Bhatia, G. S.; Peak, S. A.; Manaviazar, S. Tetrahedron Lett. 1993, 34, 5343-5346. (h) For a detailed account of our A83586C synthesis and the synthesis of other complex cyclodepsipeptides, see: Hale, K. J.; Bhatia, G. S.; Frigerio, M. The Chemical Synthesis of Natural Products; Hale, K. J., Ed.; Sheffield Academic Press: Sheffield, 2000; Chapter 12, p 349.
8. For the first total synthesis of A83586C, see: (a) Hale, K. J.; Cai, J. J. Chem. Soc. Chem. Comm. 1997, 2319. (b) Hale, K. J.; Cai, J.; Delisser, V. M. Tetrahedron Lett. 1996, 37, 9345-9348. (c) Hale, K. J.; Cai, J. Tetrahedron Lett. 1996, 37, 4233-4236. (d) Hale, K. J.; Cai, J.; Manaviazar, S.; Peak, S. A. Tetrahedron Lett. 1995, 36, 6965-6968. (e) Hale, K. J.; Delisser, V. M.; Yeh, L.-K.; Peak, S. A.; Manaviazar, S.; Bhatia, G. S. Tetrahedron Lett. 1994, 35, 7685-7688. (f) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181-9188. (g) Hale, K. J.; Bhatia, G. S.; Peak, S. A.; Manaviazar, S. Tetrahedron Lett. 1993, 34, 5343-5346. (h) For a detailed account of our A83586C synthesis and the synthesis of other complex cyclodepsipeptides, see: Hale, K. J.; Bhatia, G. S.; Frigerio, M. The Chemical Synthesis of Natural Products; Hale, K. J., Ed.; Sheffield Academic Press: Sheffield, 2000; Chapter 12, p 349.
9. For the first total synthesis of A83586C, see: (a) Hale, K. J.; Cai, J. J. Chem. Soc. Chem. Comm. 1997, 2319. (b) Hale, K. J.; Cai, J.; Delisser, V. M. Tetrahedron Lett. 1996, 37, 9345-9348. (c) Hale, K. J.; Cai, J. Tetrahedron Lett. 1996, 37, 4233-4236. (d) Hale, K. J.; Cai, J.; Manaviazar, S.; Peak, S. A. Tetrahedron Lett. 1995, 36, 6965-6968. (e) Hale, K. J.; Delisser, V. M.; Yeh, L.-K.; Peak, S. A.; Manaviazar, S.; Bhatia, G. S. Tetrahedron Lett. 1994, 35, 7685-7688. (f) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181-9188. (g) Hale, K. J.; Bhatia, G. S.; Peak, S. A.; Manaviazar, S. Tetrahedron Lett. 1993, 34, 5343-5346. (h) For a detailed account of our A83586C synthesis and the synthesis of other complex cyclodepsipeptides, see: Hale, K. J.; Bhatia, G. S.; Frigerio, M. The Chemical Synthesis of Natural Products; Hale, K. J., Ed.; Sheffield Academic Press: Sheffield, 2000; Chapter 12, p 349.
10. For the first total synthesis of A83586C, see: (a) Hale, K. J.; Cai, J. J. Chem. Soc. Chem. Comm. 1997, 2319. (b) Hale, K. J.; Cai, J.; Delisser, V. M. Tetrahedron Lett. 1996, 37, 9345-9348. (c) Hale, K. J.; Cai, J. Tetrahedron Lett. 1996, 37, 4233-4236. (d) Hale, K. J.; Cai, J.; Manaviazar, S.; Peak, S. A. Tetrahedron Lett. 1995, 36, 6965-6968. (e) Hale, K. J.; Delisser, V. M.; Yeh, L.-K.; Peak, S. A.; Manaviazar, S.; Bhatia, G. S. Tetrahedron Lett. 1994, 35, 7685-7688. (f) Hale, K. J.; Manaviazar, S.; Delisser, V. M. Tetrahedron 1994, 50, 9181-9188. (g) Hale, K. J.; Bhatia, G. S.; Peak, S. A.; Manaviazar, S. Tetrahedron Lett. 1993, 34, 5343-5346. (h) For a detailed account of our A83586C synthesis and the synthesis of other complex cyclodepsipeptides, see: Hale, K. J.; Bhatia, G. S.; Frigerio, M. The Chemical Synthesis of Natural Products; Hale, K. J., Ed.; Sheffield Academic Press: Sheffield, 2000; Chapter 12, p 349.
11. Hale, K. J.; Cai, J.; Delisser, V.; Manaviazar, S.; Peak, S. A.; Bhatia, G. S.; Collins, T. C.; Jogiya, N. Tetrahedron 1996, 52, 1047.
12. 2: Boissonnas, R. A.; Guttman, St.; Jaquenoud, P. A. Helv. Chim. Acta 1960, 43, 1349. (b) For the use of TrocNHNH2/DCC to make Troc acyl hydrazides, see: Fujii, N.; Yajima, H. J. Chem. Soc., Parkin Trans. 1, 1981, 804.
13. 2: Boissonnas, R. A.; Guttman, St.; Jaquenoud, P. A. Helv. Chim. Acta 1960, 43, 1349. (b) For the use of TrocNHNH2/DCC to make Troc acyl hydrazides, see: Fujii, N.; Yajima, H. J. Chem. Soc., Parkin Trans. 1, 1981, 804.
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15. 6 at rt for 2 h and used without purification after removal of the solvent and excess reagent in vacuo.
16. AgCN-mediated N-acylation: Durette, P. L.; Baker, F.; Barker, P. L.; Boger, J.; Bondy, S. S.; Hammond, M. L.; Lanza, T. J.; Pessalano, A.; Caldwell, C. G. Tetrahedron Lett. 1990, 31, 1237.
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18. It is important not to prolong the heating of this reaction much beyond the 3-5 min time frame we have recommended; otherwise, decomposition ensues.
19. Cheung, H. T.; Blout. E. R. J. Org. Chem. 1965, 30, 315.
20. Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4937.
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23. For the occurrence of a similar O-to N-acyl shift during removal of a Z-group from an acylated β-hydroxyleucine residue, see the Merck L-156,602 synthesis referred to in ref 8.
24. 2O/MeOH, when these solvents are subsequently removed on the rotary evaporator. Given that these hydrochloride salts are usually obtained in a fairly pure condition after hydrogenation, we recommend that they be used directly for subsequent couplings without any further purification.