4-0-Tf0-2,3-anhydro-β-L-ribopyranosides as chiron: A formal synthesis of canadensolide

Tetrahedron Letters

Volumn 37, Issue 48, 1996, Pages 8641-8642

  Al Abed, Yousef ^a,b   Naz, Noshena ^a   Mootoo, David ^c   Voelter, Wolfgang ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

^b PICOWER INST FOR MEDICAL RESEARCH   (United States)

^c CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; CANADENSOLIDE; MONOSACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; METHODOLOGY; REACTION ANALYSIS;

CHIRON;

EID: 0030602153     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02026-6     Document Type: Article

References (14)

1. 1. (a) Al-Abed, Y.; Zaman, F.; Shekhani, M. S.; Fatima, A.; Voelter, W. Tetrahedron Lett. 1992, 33, 3305.
2. (b) Al-Abed, Y.; Al-Tel, T.; Voelter, W. Tetrahedron 1993, 49, 9295.
3. 2. McCorkindale, N. J.; Wright, J. L. C.; Brain, P. W.; Clarke, S. M.; Hutchinson, S. A. Tetrahedron Lett 1968, 6, 727.
4. 3. (a) Bruke, S. D.; Pacofsky, G. J.; 'Piscopio, A. D. J. Org. Chem. 1992, 57, 2228.
5. (b) Anderson, R. C.; Fraser-Reid, B. J. Org. Chem. 1985, 50, 4781.
6. (c ) Anderson, R. C.; Fraser-Reid, B. Tetrahedron Lett. 1978, 3233.
7. (d) Ohrui, H.; Emoto, S. Tetrahedron Lett. 1975, 3657.
8. (e) kato, M.; Kageyama, M.; Tanaka, R.; Kuwahara, K.; Yoshikoshi, A. J. Org. Chem. 1975, 40, 1932.
9. 4. Honda, T.; Kobayashi, Y.; Tsubuki, M. Tetrahedron 1993, 49, 1211 and references cited in.
10. 5. Nubbemeyer, U. Synthesis 1993, 1120.
11. 6. Suginome, M.; Yamamoto, Y.; Fujii, K.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 9608.
12. 7. Isolated yield after Chromatographic purification of the crude reaction mixture. The purification has not yet been optimized. The actual yield was much higher as indicated by a 90% yield of the diacetate derivative which was obtained through acetylation of the crude product.
13. 8. Ohrui, H.; Sueda, N.; Kuzuhara, H.; Nippon Kagaku Kaishi, 1981, 769.
14. 9. The spectroscopic data of compound 8 are identical with those reported in references 4 and 8.