Novel short-step synthesis of optically active tetronic acids from chiral α-hydroxy acids mediated by 1-hydroxybenzotriazole

Synlett

Volumn , Issue 10, 2002, Pages 1736-1738

  Athanasellis, Giorgos ^a   Igglessi Markopoulou, Olga ^a   Markopoulos, John ^b  

^a NATIONAL TECHNICAL UNIVERSITY OF ATHENS   (Greece)

^b UNIVERSITY OF ATHENS   (Greece)

Author keywords

1 hydroxybenzotriazole; Natural products; Tetronic acids; hydroxy acids

Indexed keywords

1 HYDROXYBENZOTRIAZOLE; 2 HYDROXYACID; 3 ETHOXYCARBONYL 5 PHENYLTETRONIC ACID; 3 METHOXYCARBONYL 5 DIMETHYLTETRONIC ACID; 3 METHOXYCARBONYL 5 PHENYLTETRONIC ACID; 3 METHOXYCARBONYLTETRONIC ACID; 4 ACETOXY 3 HYDROXY 2 METHOXYCARBONYL 4 METHYL 2 PENTENOATE; BENZOTRIAZOLE DERIVATIVE; TETRONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGENATION; OPTICAL ROTATION; REACTION ANALYSIS; REPRODUCIBILITY;

EID: 0036401657     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34248     Document Type: Article

References (19)

1. Pattenden, G. Fortschr. Chem. Org. Naturst. 1978, 35, 133.
2. Booth, P. M.; Fox, C. M. J.; Ley, S. V. J. Chem. Soc., Perkin Trans 1 1987, 121.
3. Mittra, A.; Yamashita, M.; Kawasaki, I.; Murai, H.; Yoshioka, T.; Ohta, S. Synlett 1997, 909.
4. Bourguet-Kondracki, M.-L.; Guyot, M. Tetrahedron Lett. 1999, 40, 3149.
5. Holler, U.; Konig, G. M.; Wright, A. D. J. Nat. Prod. 1997, 60, 832.
6. Clutterbuck, P. W.; Raistrick, H.; Reuter, F. Biochem. J. 1935, 29, 300.
7. Birkinshaw, J. H.; Samant, M. S. Biochem. J. 1960, 74, 369.
8. Watanabe, K.; Tanaka, T.; Fukuhara, K.; Miyairi, N.; Yonehara, H.; Umezawa, H. J. Antibiot. 1957, 10, 39.
9. Jones, R. C. F.; Duller, K. A. M.; Vulto, S. I. E. J. Chem. Soc., Perkin Trans. 1 1998, 411.
10. Schobert, R.; Muller, S.; Bestmann, H.-J. Synlett 1995, 425.
11. (a) Effenberger, F.; Syed, J. Tetrahedron: Asymmetry 1998, 9, 817.
12. (b) Buhler, H.; Bayer, A.; Effenberger, F. Chem.Eur. J. 2000, 6, 2564.
13. Mitsos, C. A.; Zografos, A. L.; Igglessi-Markopoulou, O. J. Org. Chem. 2000, 65, 5852.
14. Athanasellis, G.; Gavrielatos, E.; Igglessi-Markopoulou, O. Synlett 2001, 1653.
15. Athanasellis, G.; Gavrielatos, E.; Igglessi-Markopoulou, O. Bull. Chem. Soc. Jpn. 2002, in press.
16. 4) and concentrated in vacuo to afford either 3-substituted tetronic acids 4-6 as white solids or the C-acylation compounds 7-14 as oils. The oily products 7-14 were dissolved in methanol and treated with 10% HCI for 24 h (7 and 8) or 48 h (9-14) at r.t. to afford the corresponding tetronic acids 15-21 as white solids. The solid products were filtered off, washed with light petrol and dried in vacuo.
17. 5: C, 51.61; H, 5.38. Found: C, 51.79; H, 5.48.
18. Nolte, M. J.; Steyn, P. S.; Wessels, P. L. J. Chem. Soc., Perkin Trans. 1 1980, 1057.
19. Petroliagi, M.; Igglessi-Markopoulou, O. J. Chem. Soc., Perkin Trans. 1 1997, 3543.