Polysubstituted piperidines via iodolactonization: Application to the asymmetric synthesis of (+)-pseudodistomin D

Organic Letters

Volumn 14, Issue 7, 2012, Pages 1672-1675

  Davies, Stephen G ^a   Fletcher, Ai M ^a   Lee, James A ^a   Roberts, Paul M ^a   Russell, Angela J ^a   Taylor, Rachael J ^a   Thomson, Anthony D ^a   Thomson, James E ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ESTER; PIPERIDINE DERIVATIVE; PSEUDODISTOMIN D;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS; UROCHORDATA; X RAY CRYSTALLOGRAPHY;

ALKALOIDS; ANIMALS; CRYSTALLOGRAPHY, X-RAY; ESTERS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PIPERIDINES; STEREOISOMERISM; UROCHORDATA;

EID: 84859595481     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300209s     Document Type: Article

References (46)

1. Ishibashi, M.; Ohizumi, Y.; Sasaki, T.; Nakamura, H.; Hirata, Y.; Kobayashi, J. J. Org. Chem. 1987, 52, 450
2. Kobayashi, J.; Cheng, J. F.; Ishibashi, M.; Nakamura, H.; Ohizumi, Y.; Hirata, Y.; Walchli, M. R.; Sasaki, T. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1988, 30, 268
3. Kobayashi, J.; Naitoh, K.; Doi, Y.; Deki, K.; Ishibashi, M. J. Org. Chem. 1995, 60, 6941
4. Freyer, A. J.; Patil, A. D.; Killmer, L.; Troupe, N.; Mentzer, M.; Carte, B.; Faucette, L.; Johnson, R. K. J. Nat. Prod. 1997, 60, 986
5. Naito, T.; Yuumoto, Y.; Ninomiya, I.; Kiguchi, T. Tetrahedron Lett. 1992, 33, 4033
6. Kiguchi, T.; Yuumoto, Y.; Ninomiya, I.; Naito, T.; Deki, K.; Ishibashi, M.; Kobayashi, J. Tetrahedron Lett. 1992, 33, 7389
7. Kiguchi, T.; Yuumoto, Y.; Ninomiya, I.; Naito, T. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1992, 34, 392
8. Ishibashi, M.; Deki, K.; Kobayashi, J. J. Nat. Prod. 1995, 58, 804
9. Naito, T.; Yuumoto, Y.; Kiguchi, T.; Ninomiya, I. J. Chem. Soc., Perkin Trans. 1 1996, 3, 281
10. Kiguchi, T.; Yuumoto, Y.; Ninomiya, I.; Naito, T. Heterocycles 1996, 42, 509
11. Kiguchi, T.; Yuumoto, Y.; Ninomiya, I.; Naito, T. Chem. Pharm. Bull. 1997, 45, 1212
12. Ma, D.; Sun, H. J. Org. Chem. 2000, 65, 6009
13. Davis, F. A.; Zhang, J.; Li, Y.; Xu, H.; DeBrosse, C. J. Org. Chem. 2005, 70, 5413
14. Doi, Y.; Ishibashi, M.; Kobayashi, J. Tetrahedron 1996, 52, 4573
15. Langlois, N. Org. Lett. 2002, 4, 185
16. Tanaka, K.; Maesoba, T.; Sawanishi, H. Heterocycles 2006, 68, 183
17. Trost, B. M.; Fandrick, D. R. Org. Lett. 2005, 7, 823
18. Utsunomiya, I.; Ogawa, M.; Natsume, M. Heterocycles 1992, 33, 349
19. Knapp, S.; Hale, J. J. J. Org. Chem. 1993, 58, 2650
20. Kiguchi, T.; Ikai, M.; Shirakawa, M.; Fujimoto, K.; Ninomiya, I.; Naito, T. J. Chem. Soc., Perkin Trans. 1 1998, 893
21. Ma, D.; Sun, H. Tetrahedron Lett. 1999, 40, 3609
22. Kiguchi, T.; Okazaki, M.; Naito, T. Heterocycles 1999, 51, 2711
23. Haddad, M.; Larcheveque, M.; Tong, H. M. Tetrahedron Lett. 2005, 46, 6015
24. Leonard, N. M.; Woerpel, K. A. J. Org. Chem. 2009, 74, 6915
25. Kobayashi, J.; Ishibashi, M. Heterocycles 1996, 42, 943
26. Ninomiya, I.; Kiguchi, T.; Naito, T. The Alkaloids 1998, 50, 317
27. Kobayashi, J.; Ishibashi, M. Stud. Nat. Prod. Chem. 2000, 23, 185
28. Davies, S. G.; Ichihara, O. Tetrahedron: Asymmetry 1991, 2, 183
29. Davies, S. G.; Smith, A. D.; Price, P. D. Tetrahedron: Asymmetry 2005, 16, 2833
30. Davies, S. G.; Garrido, N. M.; Kruchinin, D.; Ichihara, O.; Kotchie, L. J.; Price, P. D.; Price Mortimer, A. J.; Russell, A. J.; Smith, A. D. Tetrahedron: Asymmetry 2006, 17, 1793
31. Davies, S. G.; Mulvaney, A. W.; Russell, A. J.; Smith, A. D. Tetrahedron: Asymmetry 2007, 18, 1554
32. Davies, S. G.; Fletcher, A. M.; Roberts, P. M. Org. Synth. 2010, 87, 143
33. Davies, S. G.; Fletcher, A. M.; Roberts, P. M.; Smith, A. D. Tetrahedron 2009, 65, 10192
34. Davies, S. G.; Iwamoto, K.; Smethurst, C. A. P.; Smith, A. D.; Rodriguez-Solla, H. Synlett 2002, 1146
35. Chippindale, A. M.; Davies, S. G.; Iwamoto, K.; Parkin, R. M.; Smethurst, C. A. P.; Smith, A. D.; Rodriguez-Solla, H. Tetrahedron 2003, 59, 3253
36. Davies, S. G.; Haggitt, J. R.; Ichihara, O.; Kelly, R. J.; Leech, M. A.; Price Mortimer, A. J.; Roberts, P. M.; Smith, A. D. Org. Biomol. Chem. 2004, 2, 2630
37. Costello, J. F.; Davies, S. G.; Ichihara, O. Tetrahedron: Asymmetry 1994, 5, 1999
38. Zhong, M. H.; Cohen, J. H.; Abdel-Magid, A. F.; Kenney, B. D.; Maryanoff, C. A.; Shah, R. D.; Villani, F. J., Jr.; Zhang, F.; Zhang, X. Tetrahedron Lett. 1999, 40, 7721
39. Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863
40. Mitsunobu, O.; Yamada, M.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1967, 40, 935
41. Mitsunobu, O.; Yamada, Y. Bull. Chem. Soc. Jpn. 1967, 40, 2380
42. Kumara Swamy, K. C.; Bhuvan Kumar, N. N.; Balaraman, E.; Pavan Kumar, K. V. P. Chem. Rev. 2009, 109, 2551
43. Blakemore, P. R.; Cole, W. J.; Kocieński, P. J.; Morley, A. Synlett 1998, 26
44. Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635
45. Gololobov, Y. G. Tetrahedron 1981, 37, 437
46. 1H NMR spectroscopic analyses in the presence of (S)-O-acetylmandelic acid and (R, S)-O-acetylmandelic acid; see: Parker, D. Chem. Rev. 1991, 91, 1441. This value is consistent with the enantiomeric purity of the lithium (S)-N-allyl-N-(α-methyl-p-methoxybenzyl)amide 12 (i.e., >99% ee) employed for the conjugate addition to α,β-unsaturated ester 1