An organotrifluoroborate-based convergent total synthesis of the potent cancer cell growth inhibitory depsipeptides kitastatin and respirantin

Organic Letters

Volumn 16, Issue 9, 2014, Pages 2322-2325

  Beveridge, Ramsay E ^a   Batey, Robert A ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMYCIN A1; BIOLOGICAL PRODUCT; BORIC ACID; DEPSIPEPTIDE; DRUG DERIVATIVE; FLUORINATED HYDROCARBON; KITASTATIN 1; LEUCINAL; LEUCINE; RESPIRANTIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ANTIMYCIN A; BIOLOGICAL PRODUCTS; BORATES; DEPSIPEPTIDES; HYDROCARBONS, FLUORINATED; LEUCINE; MOLECULAR STRUCTURE;

EID: 84899826846     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol500484f     Document Type: Article

References (34)

1. For a review of the total synthesis of selected antimicrobial and antitumor cyclic depsipeptides, see: Li, W.; Schlecker, A.; Ma, D. Chem. Commun. 2010, 46, 5403-5420
2. Kiyota, H. Top. Heterocycl Chem. 2006, 6, 181-214
3. Yang, Y.-Q.; Wu, Y. Org. Prep. Proced. Int. 2007, 39, 135-152
4. A recent asymmetric total synthesis of 14 antimycin A family members: Inai, M.; Nishi, T.; Tanaka, A.; Kaku, H.; Horikawa, M.; Tsunoda, T. Eur. J. Org. Chem. 2011, 2719-2729
5. JBIR-06: Ueda, J.-Y.; Nagai, A.; Izumikawa, M.; Chijiwa, S.; Takagi, M.; Shin-ya, K. J. Antibiot. 2008, 61, 241-244
6. JBIR-04, JBIR-05: Izumikawa, M.; Ueda, J.-Y.; Chijiwa, S.; Takagi, M.; Shin-ya, K. J. Antibiot. 2007, 60, 640-644
7. Prunustatin A and SW-163A: Umeda, Y.; Furihata, K.; Sakuda, S.; Nagasawa, H.; Ishigami, K.; Watanabe, H.; Izumikawa, M.; Takagi, M.; Doi, T.; Nakao, Y.; Shin-ya, K. Org. Lett. 2007, 9, 4239-4242 and references therein
8. Neo-antimycin: Cagliote, L.; Misiti, D.; Selva, A.; Arcamone, F.; Cassinelli, G. Tetrahedron 1969, 25, 2193-2221
9. Pettit, G. R.; Tan, R.; Pettit, R. K.; Smith, T. H.; Feng, S.; Doubek, D. L.; Richert, L.; Hamblin, J.; Weber, C.; Chapuis, J.-C. J. Nat. Prod. 2007, 70, 1069-1072
10. Pettit, G. R.; Smith, T. H.; Feng, S.; Knight, J. C.; Tan, R.; Pettit, R. K.; Hinrichs, P. A. J. Nat. Prod. 2007, 70, 1073-1083
11. The synthesis of kitastatin 1 is claimed in a patent; however, no experimental details or yields were included regarding its preparation. Pettit, G. R.; Smith, T. H.; Feng, S. U.S. Pat. Appl. 065991, 2008.
12. Configurational stability study: Rittle, K. E.; Homnich, C. F.; Ponticello, G. S.; Evans, B. E. J. Org. Chem. 1982, 47, 3016-3018
13. Batey, R. A.; Thadani, A. N.; Smil, D. V. Tetrahedron Lett. 1999, 40, 4289-4292
14. Batey, R. A.; Thadani, A. N.; Smil, D. V. Synthesis 2000, 990-998
15. Li, S.-W.; Batey, R. A. Chem. Commun. 2004, 1382-1383
16. Nowrouzi, F.; Batey, R. A. Angew. Chem., Int. Ed. 2013, 52, 892-895
17. Ramadhar, T. R.; Bansagi, J.; Batey, R. A. J. Org. Chem. 2013, 78, 10362-10368
18. Thadani, A. N.; Batey, R. A. Org. Lett. 2002, 4, 3827-3830
19. Thadani, A. N.; Batey, R. A. Tetrahedron Lett. 2003, 44, 8051-8055
20. Nowrouzi, F.; Thadani, A. N.; Batey, R. A. Org. Lett. 2009, 11, 2631-2634
21. Nowrouzi, F.; Janetzko, J.; Batey, R. A. Org. Lett. 2010, 12, 5490-5493
22. The only related example of potassium prenyltrifluoroborate carbonyl-like reactivity is an interesting Rh-catalyzed enantioselective reaction with cyclic sulfonyl-imines; see: Luo, Y.; Hepburn, H. B.; Chotsaeng, N.; Lam, H. W. Angew. Chem., Int. Ed. 2012, 51, 8309-8313
23. Takeda, K.; Akiyama, A.; Nakamura, H.; Takizawa, S.-I.; Mizuno, Y.; Takayanagi, H.; Harigaya, Y. Synthesis 1994, 1063-1066
24. Shiina, I.; Miyao, R. Heterocycles 2008, 76, 1313-1328
25. Shiina, I.; Kubota, M.; Oshiumi, H.; Hashizume, M. J. Org. Chem. 2004, 69, 1822-1830
26. Ishiyama, T.; Ahiko, T.-A.; Miyaura, N. Tetrahedron Lett. 1996, 37, 6889-6892
27. Used within 3 h of preparation according to: Rich, D. H.; Sun, E. T.; Boparai, A. S. J. Org. Chem. 1978, 43, 3624-3626
28. Rubsam, F.; Seck, S.; Giannis, A. Tetrahedron 1997, 53, 2823-2834
29. Hanessian, S.; Park, H.; Yang, R.-Y. Synlett 1997, 353-354
30. Triprenylborane: Bubnov, Y. N.; Zhun, I. V.; Klimkina, E. V.; Ignatenko, A. V.; Starikova, Z. A. Eur. J. Org. Chem. 2000, 3323-3327
31. Prenyl-9-BBN: Kramer, G. W.; Brown, H. C. J. Organomet. Chem. 1977, 132, 9-27
32. Breitfelder, S.; Schlapbach, A.; Hoffmann, R. W. Synthesis 1998, 468-478
33. Hoffmann, R. W.; Schlapbach, A. Tetrahedron 1992, 48, 1959-1968
34. Cochet, T.; Bellosta, V.; Greiner, A.; Roche, D.; Cossy, J. Synlett 2011, 1920-1922