Construction of chiral tertiary alcohol stereocenters via the [2,3]- meisenheimer rearrangement: Enantioselective synthesis of the side-chain acids of homoharringtonine and harringtonine

Journal of Organic Chemistry

Volumn 78, Issue 2, 2013, Pages 339-346

  Yang, Hua ^a   Sun, Moran ^a   Zhao, Shuguang ^a   Zhu, Ming ^a   Xie, Yangla ^a   Niu, Changling ^a   Li, Chunlin ^a  

^a ZHENGZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL TERTIARY ALCOHOLS; ENANTIOSELECTIVE SYNTHESIS; HOMOHARRINGTONINE; SIDE-CHAINS; STEREOCENTERS;

CHEMISTRY;

ORGANIC COMPOUNDS;

2 (3 HYDROXY 6,6 DIMETHYL 2 OXOTETRAHYDRO 2H PYRAN 3 YL)ACETIC SCID; 2 HYDROXY 2 (4 HYDROXY 4 METHYLPENTYL)SUCCINIC ACID; ACETIC ACID; ALCOHOL DERIVATIVE; ALKENE; HARRINGTONINE; HOMOHARRINGTONINE; SUCCINIC ACID; TERTIARY ALCOHOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; ENANTIOSELECTIVITY; MEISENHEIMER REARRANGEMENT; METHODOLOGY; SYNTHESIS;

ACIDS; ALCOHOLS; CATALYSIS; HARRINGTONINES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84872593142     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302203g     Document Type: Article

References (48)

1. Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388-401
2. Shibasaki, M.; Kanai, M. Chem. Rev. 2008, 108, 2853-2873
3. Stymiest, J. L.; Bagutski, V.; French, R. M.; Aggarwal, V. K. Nature 2008, 456, 778-782
4. Schipper, D. J.; Rousseaux, S.; Fagnou, K. Angew. Chem., Int. Ed. 2009, 48, 8343-8347
5. Reetz, M. T.; Lauterbach, E. H. Tetrahedron Lett. 1991, 32, 4481-4482
6. Enders, D.; Kempen, H. Synlett 1994, 969-971
7. Buston, J. E. H.; Coldham, I.; Mulholland, K. R. Synlett 1997, 322-324
8. Buston, J. E. H.; Coldham, I.; Mulholland, K. R. J. Chem. Soc., Perkin Trans. 1 1999, 2327-2334
9. Buston, J. E. H.; Coldham, I.; Mulholland, K. R. Tetrahedron: Asymmetry 1998, 9, 1995-2009
10. Blanchet, J.; Bonin, M.; Micouin, L.; Husson, H.-P. Tetrahedron Lett. 2000, 41, 8279-8283
11. Guarna, A.; Occhiato, E. G.; Pizzetti, M.; Scarpi, D.; Sisi, S.; van Sterkenburg, M. Tetrahedron: Asymmetry 2000, 11, 4227-4238
12. Davies, S. G.; Smyth, G. D. J. Chem. Soc., Perkin Trans. 1 1996, 2467-2477
13. Bao, H.; Qi, X.; Tambar, U. K. J. Am. Chem. Soc. 2011, 133, 1206-1208
14. For a review on this subject, see: Bao, H.; Qi, X.; Tambar, U. K. Synlett 2011, 1789-1792
15. Otto, A.; Ziemer, B.; Liebscher, J. Eur. J. Org. Chem. 1998, 2667-2672
16. The [1,3]-transfer of O-allylic hydroxylamine is a known reaction; for a related literature, see: Yamamoto, Y.; Oda, J.; Inouye, Y. J. Org. Chem. 1976, 41, 303-306
17. 1,3 strain during the [2,3]-sigmatropic rearrangement. For the pseudo-1,3-diaxial steric interaction, see: Anderson, J. C.; Ford, J. G.; Whiting, M. Org. Biomol. Chem. 2005, 3, 3734-3748
18. 1,3 strain, see: Hoffmann, R. W. Chem. Rev. 1989, 89, 1841-1860
19. Kapferer, T.; Brückner, R. Eur. J. Org. Chem. 2006, 2119-2133
20. Berhal, F.; Tardy, S.; Pérard-Viret, J.; Royer, J. Eur. J. Org. Chem. 2009, 437-443
21. Eckelbarger, J. E.; Wilmot, J. T.; Epperson, M. T.; Thakur, C. S.; Shum, D.; Antczak, C.; Tarassishin, L.; Djaballah, H.; Gin, D. Y. Chem.-Eur. J. 2008, 14, 4293-4306
22. Ancliff, R. A.; Russell, A. T.; Sanderson, A. J. Chem. Commun. 2006, 3243-3245
23. El Bialy, S. A. A.; Braun, H.; Tietze, L. F. Eur. J. Org. Chem. 2005, 2965-2972
24. Keller, L.; Dumas, F.; d'Angelo, J. Eur. J. Org. Chem. 2003, 2488-2497
25. Keller, L.; Dumas, F.; d'Angelo, J. Tetrahedron Lett. 2001, 42, 1911-1913
26. Robin, J.-P.; Dhal, R.; Dujardin, G.; Girodier, L.; Mevellec, L.; Poutot, S. Tetrahedron Lett. 1999, 40, 2931-2934
27. Yoda, H.; Nakagami, Y.; Takabe, K. Tetrahedron: Asymmetry 1994, 5, 169-172
28. Scheurer, A.; Mosset, P.; Bauer, W.; Saalfrank, R. W. Eur. J. Org. Chem. 2001, 3067-3074
29. Corey, E. J.; Palani, A. Tetrahedron Lett. 1995, 36, 3485-3488
30. Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 6676-6682
31. Fujii, T.; Itaya, T.; Matsubara, S. Chem. Pharm. Bull. 1989, 37, 1758-1763
32. Paju, A.; Kanger, T.; Pehk, T.; Eek, M.; Lopp, M. Tetrahedron 2004, 60, 9081-9084
33. Corey, E. J.; Schmidt, G. Tetrahedron Lett. 1979, 20, 399-402
34. Crimmins, M. T.; DeBaillie, A. C. J. Am. Chem. Soc. 2006, 128, 4936-4937
35. Friedrich, P.; Darley, D. J.; Golding, B. T.; Buckel, W. Angew. Chem., Int. Ed. 2008, 47, 3254-3257
36. Rodriguez, A.; Nomen, M.; Spur, B. W. Tetrahedron Lett. 1998, 39, 8563-8566
37. Powell, R. G.; Weisleder, D.; Smith, C. R. J. Pharm. Sci. 1972, 61, 1227-1230
38. Kutsumura, N.; Nishiyama, S. J. Carbohydrate. Chem. 2006, 25, 377-385
39. Kumarn, S.; Shaw, D. M.; Longbottom, D. A.; Ley, S. V. Org. Lett. 2005, 7, 4189-4191
40. Keck, G. E.; Fleming, S.; Nickell, D.; Weider, P. Synth. Commun. 1979, 9, 281-286
41. Bui, T.; Candeias, N. R.; Barbas, C. F., III. J. Am. Chem. Soc. 2010, 132, 5574-5575
42. Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2003, 132, 6038-6039
43. Peng, J.; Jiang, D.; Lina, W.; Chen, Y. Org. Biomol. Chem. 2007, 5, 1391-1396
44. Hilli, F.; White, J. M.; Rizzacasa, M. A. Tetrahedron 2011, 67, 5054-5068
45. Patel, P.; Lee, G.-J.; Kim, S.; Grant, G. E.; Powell, W. S.; Rokach, J. J. Org. Chem. 2008, 73, 7213-7218
46. Gitterman, A.; Parry, R. J.; Dufresne, R. F.; Sternbach, D. D.; Cabelli, M. D. J. Am. Chem. Soc. 1980, 102, 2074-2081
47. Kelly, T. R.; McNutt, R. W.; Montury, M.; Tosches, N. P.; Mikolajczak, K. L.; Smith, C. R.; Weisleder, D. J. Org. Chem. 1979, 44, 63-67
48. Kelly, T. R.; McKenna, J. C.; Christenson, P. A. Tetrahedron Lett. 1973, 14, 3501-3504