Differential use of anhydropyranosides for enantiopure routes to bis-γ-butyrolactones: A new approach to the frameworks of antibiotic and anticancer agents isoavenaciolide and ethisolide

Journal of Organic Chemistry

Volumn 74, Issue 13, 2009, Pages 4690-4696

  Al Tel, Taleb H ^a   Al Qawasmeh, Raed A ^b   Sabri, Salim S ^a   Voelter, Wolfgang ^c  

^a UNIVERSITY OF SHARJAH   (United Arab Emirates)

^b UNIVERSITY OF JORDAN   (Jordan)

^c UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANTI-CANCER AGENTS; BUTYROLACTONES; CHEMICAL EQUATIONS; CHEMOSELECTIVE; DEPROTECTION; DIANIONS; ENANTIOPURE; HIGH YIELD; KETOESTER; NATURAL PRODUCTS; NEW APPROACHES; PYRANOSIDES;

ESTERS; STEREOCHEMISTRY;

CHEMICAL REACTIONS;

3,4 EPOXYPYRAN; ANHYDROPYRANOSIDE; ANTIBIOTIC AGENT; ANTINEOPLASTIC AGENT; BETA OXOCARBOXYLIC ACID ESTER; BIS GAMMA BUTYROLACTONE DERIVATIVE; DIANION; ETHISOLIDE; FURAN; IDOAVENACIOLIDE; LACTONE DERIVATIVE; PYRAN; PYRANOSIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CYCLIZATION; DEPROTECTION REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION;

4-BUTYROLACTONE; ANTI-BACTERIAL AGENTS; ANTINEOPLASTIC AGENTS; ASPERGILLUS; CYCLIZATION; EPOXY COMPOUNDS; FURANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; MONOSACCHARIDES; PENICILLIUM; STEREOISOMERISM; TANDEM MASS SPECTROMETRY;

EID: 67649604283     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900192a     Document Type: Article

References (34)

1. (a) Arjona, O.; Gomez, A. M.; Lopez, J. C; Plumet, J. Chem. Rev. 2007, 107, 1919.
2. (b) Gruner, A. A. W.; Locardi, E.; Lohof, E.; Kessler, H. Chem. Rev. 2002, 102, 491.
3. Ueda, K.; Usui, T.; Nakayama, H.; Ueki, M.; Takio, K.; Ubukata, M.; Osada, H. FEBS Lett. 2002, 525, 48.
4. (a) For a Review, see: Martin, S. V.; Rodriguez, C. M.; Martin, T. Org. Prep. Proced. Int. 1998, 30, 291.
5. (b) For enantiopure syntheses using carbohydrates, see: Anderson, R. C.; Fraser-Reid, B. J. Org. Chem. 1985, 50, 4781.
6. (c) Anderson, R. C.; Fraser-Reid, B. J. Org. Chem. 1985, 50, 4786.
7. For recent publications, see: (a) Mondal, S.; Ghosh, S. Tetrahedron 2008, 64, 2359.
8. (b) Hon, Y.-S.; Chen, H.-F. Tetrahedron Lett. 2007, 48, 8611.
9. (c) Hon, Y.-S.; Hsieh, C.-H. Tetrahedron 2007, 62, 9713.
10. (d) Hon, Y.-S.; Hsieh, C.-H. Tetrahedron 2006, 62, 9713.
11. (e) Yu, C.-M.; Youn, J.; Jung, J. Angew. Chem., Int. Ed. 2006, 45, 1553.
12. (f) Liu, H.-M.; Zhang, F.; Zou, D.-P. J. Chem. Soc., Chem. Commun. 2003, 2044.
13. (g) Sharma, G. V. M.; Gopinath, T. Tetrahedron Lett. 2001, 42, 6183.
14. (h) Alcazar, E.; Kassou, M.; Matheu, I.; Castillon, S. Eur. J. Org. Chem. 2000, 65, 2285.
15. (i) Chen, M.-J.; Narkunan, K.; Liu, R.-S. J. Org. Chem. 1999, 64, 8311.
16. (j) Rodriguez, C. M.; Martin, T.; Martin, V. S. J. Org. Chem. 1996, 61, 8448.
17. (a) Naz, N.; Al-Tel, T. H.; Al-Abed, Y.; Voelter, W.; Ficker, R.; Hiller, W. J. Org. Chem. 1996, 61, 3250.
18. (b) Al-Tel, T. H.; Voelter, W. J. Chem. Soc. Chem. Commun. 1995, 239.
19. (c) Al-Tel, T. H.; Al-Abed, Y.; Voelter, W. J. Chem. Soc. Chem. Commun. 1994, 1735.
20. (d) Al-Tel, T. H.; Voelter, W. Tetrahedron Lett. 1995, 36, 523.
21. (a) Al-Tel, T. H.; Meisenbach, M.; Voelter, W. Liebigs Ann. 1995, 689.
22. (b) Al-Qawasmeh, R. A.; Al-Tel, T. H.; Abdel-Jalil, R.; Voelter, W. Chem. Lett. 1999, 541.
23. (a) Al-Abed, Y.; Al-Tel, T. H.; Voelter, W. Tetrahedron 1993, 49, 9295, and references therein.
24. (b) Grieco, P. A. Synthesis 1975, 67, 564 and relevant references therein.
25. (a) Cossy, J.; Ranaivosata, J.-L.; Bellosta, V. Tetrahedron Lett. 1994, 35, 1205.
26. (b) Honda, T.; Kobayoshi, Y.; Tsubuki, M. Tetrahedron 1993, 49, 1211.
27. (c) Burke, S. D.; Pacofsky, G. J.; Piscopio, A. D. J. Org. Chem. 1992, 57, 2228, and references therein.
28. (d) Nakunan, K.; Liu, R.-S. J. Chem. Soc. Chem. Commun. 1998, 1521 and relevant references therein.
29. Similar findings in relation to the geometry of the exo-alkylidene tetrahydrofuran derivatives have been reported by Prof. Trost: (a) Trost, B. M.; Runge, T. A. J. Am. Chem. Soc. 1981, 103, 7550.
30. (b) Trost, B. M.; Runge, T. A. J. Am. Chem. Soc. 1981, 103, 7559.
31. The adopted numbering scheme is only for the purpose of NMR interpretation (see refs 3b and 3c).
32. Motawia, M. S.; Pedersen, E. B. Liebigs Ann. 1990, 599.
33. (a) Thibaudeau, C.; Foldesi, A.; Chattopadhyaya, J. Tetrahedron 1998, 54, 1867.
34. (b) Plavec, J.; Tong, W.; Chattopadhyaya, J. J. Am. Chem. Soc. 1993, 115, 9734.