Highly efficient, enantioselective synthesis of (+)-grandisol from a C2-symmetric bis(α,β-butenolide)

Organic Letters

Volumn 2, Issue 2, 2000, Pages 163-165

  De March, Pedro ^a   Figueredo, Marta ^a   Font, Josep ^a   Raya, Javier ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

GRANDISOL; MANNITOL; SEX PHEROMONE; TERPENE;

ARTICLE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

MANNITOL; SEX ATTRACTANTS; STEREOISOMERISM; TERPENES;

EID: 0034719240     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991261k     Document Type: Article

References (15)

1. For a review see: Magnuson, S. R. Tetrahedron 1995, 51, 2167.
2. See ref 3 in: Sánchez-Sancho, F.; Valverde, S.; Herradón, B. Tetrahedron: Asymmetry 1996, 7, 3209.
3. Mann, J.; Partlett, N. K.; Thomas, A. J. Chem. Res., Synop. 1987, 369.
4. (a) Tumlinson, J. H.; Hardee, D. D.; Gueldner, R. C.; Thompson, A. C.; Hedin, P. A.; Minyard, J. P. Science 1969, 166, 1010.
5. (b) Tumlinson, J. H.; Gueldner, R. C.; Hardee, D. D.; Thompson, A. C.; Hedin, P. A.; Minyard, J. P. J. Org. Chem. 1971, 36, 2616.
6. Alibés, R.; Bourdelande, J. L.; Font, J.; Parella, T. Tetrahedron 1996, 52, 1279. See references therein for other synthetic approaches to (±)-, (+)-, and (-)-grandisol.
7. De March, P.; Figueredo, M.; Font, J.; Raya, J. Tetrahedron Lett. 1999, 40, 2205.
8. Poitout, L.; Le Merrer, Y.; Depezay, J. C. Tetrahedron Lett. 1994, 35, 3293.
9. 6: C, 53.10; H, 4.46. Found: C, 52.88; H, 4.58.
10. Figueredo, M.; Font, J.; Virgili, A. Tetrahedron 1987, 43, 1881.
11. 6: C, 51.86; H, 7.07. Found: C, 51.95; H, 7.12.
12. 6: C, 47.55; H, 6.65; N, 12.32. Found: C, 47.47; H, 6.60; N, 12.24.
13. Alibés, R.; Bourdelande, J. L.; Font, J.; Gregori, A.; Parella, T. Tetrahedron 1996, 52, 1267.
14. 6: C, 54.24; H, 7.59. Found: C, 53.93; H, 7.55.
15. 6: C, 61.92; H, 7.15. Found: C, 62.16; H, 7.34.