Total synthesis of (-)-belactosin C and derivatives via double diastereoselective tandem mukaiyama aldol lactonizations

Organic Letters

Volumn 9, Issue 8, 2007, Pages 1537-1540

  Sung, Wook Cho ^a   Romo, Daniel ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3-HYDROXYBUTANAL; ACETAL DERIVATIVE; ALDEHYDE; ALDOL; BELACTOSIN C; DIPEPTIDE; GLYOXAMIDE; KETONE; LACTONE; PEPTIDE; SULFONYLUREA DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ACETALS; ALDEHYDES; DIPEPTIDES; KETONES; LACTONES; MOLECULAR STRUCTURE; PEPTIDES; STEREOISOMERISM; SULFONYLUREA COMPOUNDS;

EID: 34247490224     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070275k     Document Type: Article

References (30)

1. (a) Mizukami, T.; Asai, A.; Yamashita, Y.; Katahira, R.; Hasegawa, A.; Ochiai, K.; Akinaga, S. U.S. Patent 5 663 298, 1997;
2. Chem. Abstr. 1997, 126, 79.
3. (b) Asai, A.; Hasegawa, A.; Ochiai, K.; Yamashita, Y.; Mizukami, T. J. Antibiot. 2000, 53, 81.
4. (c) Yamaguchi, H.; Asai, A.; Mizukami, T.; Yamashita, Y.; Akinaga, S.; Ikeda, S.-i.; Kanda, Y. EP Patent 1 166 781 A1, 2000;
5. Chem. Abstr. 2000, 133, 751.
6. Asai, A.; Tsujita, T.; Sharma, S. V.; Yamashita, Y.; Akinaga, S.; Funakoshi, M.; Kobayashi, H.; Mizukami, T.; Asahi-machi, M.-S. Biochem. Pharmacol. 2004, 67, 227.
7. Groll, M.; Larionov, O. V.; Huber, R.; De Meijere, A. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 4576.
8. (a) Yang, H. W.; Romo, D. J. Org. Chem.. 1997, 62, 4.
9. (b) Yang, H. W.; Zhao, C.; Romo, D. Tetrahedron 1997, 53, 16471.
10. (c) Wang, Y.; Zhao, C.; Romo, D. Org. Lett. 1999, 1, 1197.
11. (a) Dollinger, L. M.; Howell, A. R. J. Org. Chem. 1996, 61, 7248.
12. (b) Yin, J.; Yang, X. B.; Chen, Z. X.; Zhang, Y. H. Chin. Chem. Lett. 2005, 16, 1448.
13. Ma, G.; Zancanella, M.; Oyola, Y.; Richardson, R. D.; Smith, J. W.; Romo, D. Org. Lett. 2006, 8, 4497.
14. Zemribo, R.; Champ, M. S.; Romo, D. Synlett 1996, 278.
15. Schmitz, W. D.; Messerschmidt, B.; Romo, D. J. Org. Chem. 1998, 63, 2058.
16. (a) Armstrong, A.; Scutt, J. N. Chem. Commun. 2004, 5, 510.
17. (b) Arionov, O. V.; de Meijere, A. Org. Lett. 2004, 6, 2153.
18. (c) Kumaraswamy, G.; Padmaja, M.; Markondaiah, B.; Jena, N.; Sridhar, B.; Kiran, M. U. J. Org. Chem. 2006, 71, 337.
19. (a) Begis, G.; Sheppard, T. D.; Cladingboel, D. E.; Motherwell, W. B.; Tocher, D. A. Synthesis 2005, 19, 3186.
20. (b) Larionov, O. V.; Kozhushkov, S. I.; Brandi, M.; de Meijere, A. Mendeleev Commun. 2003, 5, 199.
21. (c) Jain, R. P.; Vederas, J. C. Org. Lett. 2003, 5, 4669.
22. (d) Armstrong, A.; Scutt, J. Org. Lett. 2003, 5, 2331.
23. (e) Brandl, M.; Kozhushkov, S.; Loscha, K.; Kokoreva, O.; Yufit, D.; Howard, J.; de Meijere, A. Synlett 2000, 1741.
24. For a review describing the use of chiral glyoxals in synthesis, see: Whitesell, J. Chem. Rev. 1992, 92, 953.
25. Doldouras, G. A.; Kollonitsch, J. J. Am. Chem. Soc. 1978, 100, 341.
26. For the synthesis of a related phenylthio ketene acetal. see ref 9b.
27. β-Lactone benzyl esters were previously utilized by Yamaguchi and co-workers in this context. See ref 1c.
28. Prasad, K. R.; Chandrakumar, A. Synthesis 2006, 2159.
29. See Supporting Information for details.
30. Another synthesis of belactosin C appeared while this manuscript was under review. See: Kumaraswamy, G.; Markondaiah, B. Tetrahedron Lett. 2007, 48, 1707.