Stereoselective divergent synthesis of four diastereomers of pachastrissamine (Jaspine B)

Journal of Organic Chemistry

Volumn 75, Issue 11, 2010, Pages 3843-3846

  Yoshimitsu, Yuji ^a   Inuki, Shinsuke ^a   Oishi, Shinya ^a   Fujii, Nobutaka ^a   Ohno, Hiroaki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BOC GROUP; DIASTEREOMERS; DIVERGENT SYNTHESIS; PACHASTRISSAMINE (JASPINE B); PHYTOSPHINGOSINES; STEREO-SELECTIVE; STEREOGENIC CENTERS; STEREOSPECIFIC RING; TOSYLATION;

ALDEHYDES; CYCLIZATION;

SYNTHESIS (CHEMICAL);

2 EPIPACHASTRISSAMINE; 2,3 EPIPACHASTRISSAMINE; 3 EPIPACHASTRISSAMINE; ALDEHYDE; PHYTOSPHINGOSINE; SPHINGOSINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; RING OPENING; STEREOCHEMISTRY;

ALDEHYDES; CYCLIZATION; SPHINGOSINE; STEREOISOMERISM; TOSYL COMPOUNDS;

EID: 77953014231     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1005284     Document Type: Article

References (35)

1. Kuroda, I.; Musman, M.; Ohtani, I.; Ichiba, T.; Tanaka, J.; Garcia-Gravalos, D.; Higa, T. J. Nat. Prod. 2002, 65, 1505-1506
2. Ledroit, V.; Debitus, C.; Lavaud, C.; Massoit, G. Tetrahedron Lett. 2003, 44, 225-228
3. Salma, Y.; Lafont, E.; Therville, N.; Carpentier, S.; Bonnafé, M. J.; Levade, T.; Génisson, Y.; Abadie, N. A. Biochem. Pharmacol. 2009, 78, 477-485
4. Canals, D.; Mormeneo, D.; Fabriàs, G.; Llebaria, A.; Casas, J.; Delgado, A. Bioorg. Med. Chem. 2009, 17, 235-241
5. For previous syntheses, see: Sudhakar, N.; Kumar, A. R.; Prabhakar, A.; Jagadeesh, B.; Rao, B. V. Tetrahedron Lett. 2005, 46, 325-327
6. Bhaket, P.; Morris, K.; Stauffer, C. S.; Datta, A. Org. Lett. 2005, 7, 875-876
7. van den Berg, R.; Boltje, T.; Verhagen, C.; Litjens, R.; Vander Marel, G.; Overkleeft, H. J. Org. Chem. 2006, 71, 836-839
8. Du, Y.; Liu, J.; Linhardt, R. J. J. Org. Chem. 2006, 71, 1251-1253
9. Liu, J.; Du, Y.; Dong, X.; Meng, S.; Xiao, J.; Cheng, L. Carbohydr. Res. 2006, 341, 2653-2657
10. Ribes, C.; Falomir, E.; Carda, M.; Marco, J. A. Tetrahedron 2006, 62, 5421-5425
11. Lee, T.; Lee, S.; Kwak, Y. S.; Kim, D.; Kim, S. Org. Lett. 2007, 9, 429-432
12. Reddy, L. V. R.; Reddy, P. V.; Shaw, A. K. Tetrahedron: Asymmetry 2007, 18, 542-546
13. Ramana, C. V.; Giri, A. G.; Suryawanshi, S. B.; Gonnade, R. G. Tetrahedron Lett. 2007, 48, 265-268
14. Prasad, K. R.; Chandrakumar, A. J. Org. Chem. 2007, 72, 6312-6315
15. Abraham, E.; Candela-Lena, J. I.; Davies, S. G.; Georgiou, M.; Nicholson, R. L.; Roberts, P. M.; Russell, A. J.; Snchez-Fernndez, E. M.; Smith, A. D.; Thomson, J. E. Tetrahedron: Asymmetry 2007, 18, 2510-2513
16. Yakura, T.; Sato, S.; Yoshimoto, Y. Chem. Pharm. Bull. 2007, 55, 1284-1286
17. Abraham, E.; Brock, E. A.; Candela-Lena, J. I.; Davies, S. G.; Georgiou, M.; Nicholson, R. L.; Perkins, J. H.; Roberts, P. M.; Russell, A. J.; Snchez-Fernndez, E. M.; Scott, P. M.; Smith, A. D.; Thomson, J. E. Org. Biomol. Chem. 2008, 6, 1665-1673
18. Passiniemi, M.; Koskinen, A. M. P. Tetrahedron Lett. 2008, 49, 980-983
19. Venkatesan, K.; Srinivasan, K. V. Tetrahedron: Asymmetry 2008, 19, 209-215
20. Enders, D.; Terteryan, V.; Palecek, J. Synthesis 2008, 2278-2282
21. Ichikawa, Y.; Matsunaga, K.; Masuda, T.; Kotsuki, H.; Nakano, K. Tetrahedron 2008, 64, 11313-11318
22. Reddipalli, G.; Venkataiah, M.; Mishra, M. K.; Fadnavis, N. W. Tetrahedron: Asymmetry 2009, 20, 1802-1805
23. Inuki, S.; Yoshimitsu, Y.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2009, 11, 4478-4481
24. Jayachitra, G.; Sudhakar, N.; Ravi Kumar Anchoori, B.; Venkateswara, R.; Sayantani, R.; Rajkumar, B. Synthesis 2010, 115-119
25. For a review, see: Abraham, E.; Davies, S. G.; Roberts, P. M.; Russell, A. J.; Thomson, J. E. Tetrahedron: Asymmetry 2008, 19, 1027-1047
26. 2O).
27. Garner, P. Tetrahedron Lett. 1984, 25, 5855-5858
28. Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. Synthesis 1998, 1707-1709
29. For the synthesis of pachastrissamine derivatives from Garners aldehyde, see refs 2a 2n, and 2s.
30. For the pioneering work on the Lewis acid-mediated THF ring formation of triol derivatives via orthoester formation, see: Zheng, T.; Narayan, R. S.; Schomaker, J. M.; Borhan, B. J. Am. Chem. Soc. 2005, 127, 6946-6947
31. Formation of unidentified byproduct was observed. Protection of the primary hydroxy group as silyl ether (18, Scheme 7) suppressed formation of the side products to give 20 in excellent yield.
32. The reaction of the corresponding silyl ether 26 with t -BuOK gave the silyl migration products 27 and 28 (see the Supporting Information).
33. A related oxazinanone formation was reported; see: Komatsu, Y.; Ikishima, H.; Okuyama, A.; Nakamura, M.; Kotsuki, H. Synth. Org. Chem. Jpn. 2009, 67, 65-75
34. Tanabe, Y.; Yamamoto, H.; Yoshida, Y.; Miyawaki, T.; Utsumi, N. Bull. Chem. Soc. Jpn. 1995, 68, 297-300
35. For a related THF formation under acidic conditions, see: Armin, B.; Jens, H.; Jacques, W.; Henri, B. K. J. Org. Chem. 1993, 58, 6814-6817