Highly diastereoselective desymmetrizations of cyclo(Pro,Pro): An enantioselective strategy toward phakellstatin and phakellin

Organic Letters

Volumn 4, Issue 16, 2002, Pages 2645-2648

  Poullennec, Karine G ^a   Kelly, Anna T ^a   Romo, Daniel ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHAKELLIN; PHAKELLSTATIN; PIPERAZINE DERIVATIVE; PROLINE;

ARTICLE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; MAGNETIC RESONANCE SPECTROSCOPY; PIPERAZINES; PROLINE; STEREOISOMERISM;

EID: 0037043548     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026140q     Document Type: Article

References (37)

1. (a) Faulkner, D. J. Nat. Prod. Rep. 2000, 17, 1-6.
2. (b) Faulkner, D. J. Nat. Prod. Rep. 2000, 17, 7-55.
3. (c) Jaspars, M. Chem. Ind. 1999, 51-55.
4. Potier, P.; Mourabit, A. A. Eur. J. Org. 2001, 237-243.
5. Sharma, G. M.; Burkholder, P. R. J. Chem. Soc., Chem. Commun. 1971, 151-152.
6. Pettit, G. R.; McNulty, J.; Herald, D. L.; Doubek, D. L.; Chapuis, J.-C.; Schmidt, J. M.; Tackett, L. P.; Boyd, M. R. J. Nat. Prod. 1997, 60, 180-183.
7. Foley, L. H.; Buchi, G. J. Am. Chem. Soc. 1982, 104, 1777-1779.
8. Dilley, A. S.; Romo, D. Org. Lett. 2001, 3, 1535-1538.
9. Kinnel, R. B.; Gehrken, H.-P.; Swali, R.; Skoropowski, G.; Scheuer, P. J. J. Org. Chem. 1998, 63, 3281-3286. These authors propose that phakellin may be responsible for the potent but never identified antibiotic activity in crude extracts of Phakellia flabellata.
10. For another strategy to these compounds, see: Jacquot, D. E. N.; Hoffmann, H.; Polborn, K.; Lindel, T. Tetrahedron Lett. 2002, 43, 3699-3702.
11. Ishibashi, N.; Kouge, K.; Shinoda, I.; Kanehisa, H.; Okai, H. Agric. Biol. Chem. 1988, 3, 819-827.
12. For electrophilic additions to DKP enolates see (a) Öhler, E.; Tataruch, F.; Schmidt, U. Chem. Ber. 1972, 105, 3658-3661.
13. (b) Williams, R. M.; Kwast, A. J. Org. Chem. 1988, 53, 5787-5789.
14. (c) Williams, R. M.; Glinka, T.; Kwast, E. J. Am. Chem. Soc. 1988, 110, 5927-5929.
15. (d) Kishi, Y.; Fukuyama, T.; Nakatsuka, S. J. Am. Chem. Soc. 1973, 95, 6490-6492.
16. (e) Kishi, Y.; Fukuyama, T.; Nakatsuka, S. J. Am. Chem. Soc. 1973, 95, 6492-6493.
17. (f) Kishi, Y.; Fukuyama, T.; Nakatsuka, S.; Havel, M. J. Am. Chem. Soc. 1973, 95, 6493-6495.
18. (g) Williams, R. M.; Anderson, O. P.; Armstrong, R. W.; Josey, J.; Meyers, H.; Eriksson, C. J. Am. Chem. Soc. 1982, 104, 6092-6099.
19. For diastereoselective alkylations of related systems see: (a) Martín-Santamaría, S.; Buenadicha, F. L.; Espada, M.; Söllhuber, M.; Avendaño, C. J. Org. Chem. 1997, 62, 6424-6428.
20. (b) Martín-Santamaría, S.; Espada, M.; Avendaño, C. Tetrahedron 1997, 53, 16795-16802.
21. For alkylations of cyclo(Pro, Pro), see: (a) Schmidt, U. Nikitorov, A. Monatsch. Chem. 1975, 106, 313-320.
22. (b) Schmidt, U.; Poisel, H. Chem Ber. 1973, 106, 3408-3420.
23. (c) Öhler, E.; Poisel, H.; Tataruch, F.; Schmidt, U. Chem. Ber. 1972, 105, 625-634.
24. (d) Poisel, H.; Schmidt, U. Chem. Ber. 1972, 105, 635-641.
25. (a) Schöllkopf, U.; Tiller, T.; Bardengen, J. Tetrahedron 1988, 44, 5293-5305.
26. (b) Rjappa, S.; Natekar, M. V. Adv. Het. Chem. 1993, 57, 187-289.
27. (a) Groaning, M. D.; Meyers, A. I. Tetrahedron 2000, 56, 9843-9873 and references cited herein.
28. (b) Meyers, A. I.; Seefeld, M. A.; Lefker, B. A.; Blake, J. R. J. Am. Chem. Soc. 1997, 119, 4565-4566.
29. (c) Meyers, A. I.; Seefeld, M. A.; Lefker, B. A.; Blake, J. F.; Willard, P. G. J. Am. Chem. Soc. 1998, 120, 7429-7438. For studies on pyramidalization of trigonal centers see:
30. (d) Seebach, D.; Maetzke, T.; Petter, W.; Klotzer, B.; Plattner, D. A. J. Am. Chem. Soc. 1991, 113, 1781-1786.
31. (e) Seebach, D.; Juaristi, E.; Miller, D. D.; Schickli, C.; Weber, T. Helv. Chim. Acta 1987, 70, 237-261.
32. Ando, K.; Green, N. S.; Li, Y.; Houk, K. N. J. Am. Chem. Soc. 1999, 121, 5334-5335.
33. Durkin, K. A.; Liotta, D. J. Am. Chem. Soc. 1990, 112, 8162-8163.
34. Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011-4030.
35. Kim, K.; Qian, L. Tetrahedron Lett. 1993, 34, 7677-7680.
36. It has been demonstrated using NMR and X-ray crystallography that aromatic systems are folded over DKP ring system, see ref 13b. Moreover, the upfield shift of H-6 in benzyl DKP 6f and carbobenzyloxy DKP 6c suggests that the aromatic rings are indeed folded over the DKP in solution.
37. While this manuscript was in review, an approach to racemic dibromophakellstatin and dibromoisophakellin was recently described: Wiese, K. J.; Yakushijin, K.; Home, D. A. Tetrahedron Lett. 2002, 43, 5135-5136.