The first enantioselective synthesis of (-)-microcionin 2

Tetrahedron Asymmetry

Volumn 7, Issue 10, 1996, Pages 2821-2824

  Potvin, Steeves ^a   Canonne, Perséphone ^a  

^a UNIVERSITÉ LAVAL   (Canada)

Author keywords

( ) microcionin 2; (R) (+) 4 methylcyclohex 2 en 1 one; 2 (3 furyl)ethyl bromide; Rieke magnesium

Indexed keywords

MICROCIONIN 2; TERPENOID; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030272151     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00371-0     Document Type: Article

References (17)

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2. 2. Cimino, G.; De Rosa, S.; De Stefano, S.; Morrone, R and Sodano, G. Tetrahedron 1985, 41, 1093.
3. 3. Hellou, J.; Andersen, R.J. and Thompson, J.E. Tetrahedron 1982, 38, 1875.
4. 4. Angers, P. and Canonne, P. Tetrahedron Lett. 1995, 36, 2397.
5. 5. Siems, K.; Jakupovic, J; Castro, V. and Poveda, L. Phytochemistry 1996, 41, 851.
6. 6. Barieux, J.-J. and Gore, J. Bull. Soc. chim. Fr. 1971, 3978.
7. 7. Silvestri, M.G. J. Org. Chem. 1983, 45, 2419.
8. 8. Lee, H.W.; Ji, S.K.; Lee, I.-Y.C. and Lee, J.H. J. Org. Chem 1996, 61, 2542.
9. D = +113 (c = 1.41,CHCl3)).
10. 2,76% v: Mg Rieke, THF.
11. 11. Tanis, S.P. and Herrinton, P.M. J. Org. Chem. 1985, 50, 3988.
12. 12. The formation of the Grignard reagent 7 is highly dependant on solvent and on the type of magnesium.
13. 13. Solution of 2.5 g of Rieke® Magnesium in 50 mL of THF. Rieke Metals Inc., 6133 Heide Lane, Lincoln, Nebraska 68512, Tel & Fax (402) 472-9044.
14. 14. Danifshefsky, S.; Chackalamannil, S.; Harrison, P.; Silvestri, M.G. and Cole, P. J. Am. Chem. Soc. 1985, 107, 2474.
15. 2: C, 76.44; H, 7.90. Found: C, 76.55; H, 8.29.
16. 3): δ 215.1, 142.7, 138.4, 126.1, 110.8, 50.0, 43.4, 37.0, 36.8, 34.4, 29.4, 21.1, 18.5, 14.1, 9.2.
17. 4.