A carbohydrate-based synthetic approach to quadrone

Tetrahedron Letters

Volumn 38, Issue 34, 1997, Pages 5975-5976

  Ermolenko, Mikhail S ^a   Pipelier, Muriel ^a  

^a INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; QUADRONE; SESQUITERPENE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030825430     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01347-6     Document Type: Article

References (11)

1. Smith III, A. B.; Konopelsky, J. P.; Wexler, B. A.; Sprengeler, P. A. J. Am. Chem. Soc. 1991, 113, 3533-3542 and references cited therein.
2. Ermolenko, M. S.; Olesker, A.; Lukacs, G. Tetrahedron Lett. 1994, 35, 711-714.
3. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287.
4. Meyer, S. D.; Schreiber, S. L. J. Org. Chem. 1994, 59, 7549-7552.
5. (a) Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183-2186;
6. (b) Pipelier, M.; Ermolenko, M. S.; Zampella, A.; Olesker, A.; Lukacs, G. Synlett 1996, 24-26.
7. Behling, J. R.; Babiak, K. A.; Ng, J. S.; Campbell, A. L.; Moretti, R.; Koerner, M.; Lipshutz, B. H. J. Amer. Chem. Soc. 1988, 110, 2641-2643.
8. Both 8 and its epimer are synthetically useful since the carbinol centre is to be oxidized later on.
9. At first, as an element of the bicyclic skeleton providing the highly stereoselective introduction of the side chains at C-2 and C-4, and later, as an anchor group preserving these centres from easy isomerization (see 5×6 above).
10. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron, 1985, 41, 3901-3924.
11. 3 solutions. Selected data: 3: +58 (c 1.0); 5: +46 (c 1.0); 6: +27 (c 0.9); 7: -31 (c 2.0); 8: +50 (c 1.3); 9: +41 (c 1.3); 11: +61 (c 1.5); 12: +52 (c 0.9); 13: -30 (c 0.5).