Improved enantioselective synthesis of natural striatenic acid and its methyl ester

Tetrahedron Letters

Volumn 47, Issue 22, 2006, Pages 3669-3671

  Aubin, Yoann ^a   Audran, Gérard ^a   Monti, Honoré ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

(+) (2R,5R) trans Dihydrocarvone; Enantioselective synthesis; Natural products; Striatenic acid

Indexed keywords

ESTER; NATURAL PRODUCT; STRIATENIC ACID; UNCLASSIFIED DRUG;

ARTICLE; ENANTIOSELECTIVITY; LIVERWORT; SYNTHESIS;

CHEILOLEJEUNEA;

EID: 33646117980     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.03.147     Document Type: Article

References (19)

1. Tori M., Aiba A., Koyama H., Hashimoto T., Nakashima K., Sono M., and Asakawa Y. Tetrahedron 56 (2000) 1655-1659
2. Audran G., Galano J.-M., and Monti H. Eur. J. Org. Chem. (2001) 2293-2296
3. Uttaro J.-P., Audran G., Palombo E., and Monti H. J. Org. Chem. 68 (2003) 5407-5410
4. Palombo E., Audran G., and Monti H. Tetrahedron Lett. 44 (2003) 6463-6464
5. Palombo E., Audran G., and Monti H. Synlett (2005) 2104-2106
6. Palombo E., Audran G., and Monti H. Tetrahedron 61 (2005) 9545-9549
7. 4 led to (+)-(R)-6-methylcyclohex-2-en-1-one (. Solladié G., and Hutt J. J. Org. Chem. 52 (1987) 3560-3566 )
8. (b) Treatment of this ketone with methyllithium, followed by oxidation with pyridinium chlorochromate (PCC), afforded (+)-3 (. Iio H., Monden M., Okada K., and Tokoroyama T. J. Chem. Soc., Chem. Commun. (1987) 358-359
9. See also:. Dauben W.G., and Michno D.M. J. Org. Chem. 42 (1977) 682-685 ). {A figure is presented}
10. Ziegler F.E., and Wender P.A. Tetrahedron Lett. (1974) 449-452
11. Ziegler F.E., Reid G.R., Studt W.L., and Wender P.A. J. Org. Chem. 42 (1977) 1991-2001
12. Cory R.M., Burton L.P.J., Chan D.M.T., McLaren F.R., Rastall M.H., and Renneboog R.M. Can. J. Chem. 62 (1984) 1908-1921
13. Safaryn J.E., Chiarello J., Chen K.M., and Joullie M.M. Tetrahedron 42 (1986) 2635-2642
14. Mander L.N., and Sethi P. Tetrahedron Lett. 24 (1983) 5425-5428
15. 3: C, 67.89; H, 9.50. Found: C, 68.07; H, 9.53.
16. 2: C, 76.88; H, 9.46. Found: C, 76.53; H, 9.49.
17. 2ZrHCl (Schwartz reagent) was unfitted for our synthetic sequence [. Godfrey A.G., and Ganem B. Tetrahedron Lett. 33 (1992) 7461-7464 ]
18. Soderquist J.A., and Ramos-Veguilla J. In: Paquette L.A. (Ed). Encyclopedia of Reagents for Organic Synthesis Vol. 5 (1995), John Wiley & Sons, Chichester 3363-3365
19. The high enantiomeric purity of (+)-2 was verified by chiral HPLC [>98% ee; Chiralpak AD (250 × 4.6 mm) column, hexane, 1 mL/min].