A short and selective synthesis of (S)-geranylcitronellol via conjugate addition of a functionalized copper reagent to 2-substituted exo-bornyl crotonates

Tetrahedron Letters

Volumn 37, Issue 39, 1996, Pages 7127-7128

  Johansson, Anders ^a   Olsson, Thomas ^a,c   Bergström, Gunnar ^b  

^a CHALMERS UNIVERSITY OF TECHNOLOGY   (Sweden)

^b UNIVERSITY OF GOTHENBURG   (Sweden)

^c ASTRAZENECA R AND D   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE; GERANYLCITRONELLOL; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030599227     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01557-2     Document Type: Article

References (25)

1. 1. Presented in part at OMCOS 8 (Organometatlic Chemistry Directed Towards Organic Synthesis) August 7-10 1995 in Santa Barbara, Calif., USA
2. 2. a. Kullenberg, B.; Bergström, G.; Bringer, B.; Carlberg, B.; Cederberg, B.; Zoon Suppl. 1973, 1, 23-32.
3. b. Bergström, G.; Svensson, B.G.; Appelgren, M.; Groth, I. Biosystematics of Social Insects; Howse, P.E.; Clement, J.-L. Eds; Acad. Press 1981, 175-183.
4. c.Ahlquist, L.; Bergström, G.; Liljenberg, C. Prog. Chem. Fats other Lipids 1978, 16, 231-255.
5. 3. a. Bergdahl, M.; Nilsson, M.; Olsson, T.; Stem, K. Tetrahedron 1991, 47, 9691-9702.
6. b. Bergdahl, M.; Nilsson, M.; Olsson, T. J. Organomet. Chem. 1990, 391, C19-C22.
7. c. Somfai, P.; Tanner, D.; Olsson, T. Tetrahedron 1985, 41, 5973-5980.
8. 4. a. Eriksson, M.; Hjelmencrantz, A.; Nilsson, M.; Olsson, T. Tetrahedron 1995, 51, 12631-12644.
9. b. Eriksson, M.; Nilsson, M.; Olsson, T. Synlett 1994, 271-272.
10. c. Bergdahl, M.; Eriksson, M.; Nilsson, M.; Olsson, T. J. Org. Chem. 1993, 58, 7238-7244.
11. d. Bergdahl, M.; Lindstedt, E.-L; Nilsson, M.; Olsson, T. Tetrahedron 1989, 45, 535-543.
12. e. Ibid. 1988, 44, 2055-2062.
13. f. Bergdahl, M.; Lindstedt, E.-L. J. Organomet. Chem. 1989, 365, C11-C14.
14. f=0.34, 5% ether/pentane, 6 g sil7ica gel) gave 180 mg (69%) homoallyladduct 4b.
15. 6. The iodide 3 was prepared following a route reported for homoallylic bromides: Bury, P.; Hareau, G.; Kocienski, P.; Dhank, D, Tetrahedron 1994, 50, 8793-8808. For other syntheses of 3, see a. Dodd, D.S.; Oehlschlager, A.C. J. Org. Chem. 1992, 57, 2794-2803.
16. 6. The iodide 3 was prepared following a route reported for homoallylic bromides: Bury, P.; Hareau, G.; Kocienski, P.; Dhank, D, Tetrahedron 1994, 50, 8793-8808. For other syntheses of 3, see a. Dodd, D.S.; Oehlschlager, A.C. J. Org. Chem. 1992, 57, 2794-2803.
17. b. Kocienski, P.; Wadman, S. J. Org Chem. 1989, 54, 1215-1217.
18. 7. a. Corey, E.J.; Beames, D.J. J. Am. Chem. Soc. 1972, 94, 7210-7211.
19. b. Seebach, D.; Neumann, H. Chem. Ber. 1974, 107, 847-853.
20. 8. a. Bailey, W.F.; Punzalan, E.R. J. Org. Chem. 1990, 55, 5404-5406.
21. b. Negishi, E.; Swanson, D.R.; Rousset, C.J. J. Org. Chem. 1990, 55, 5406-5409.
22. 2c
23. 2c [α]D-3.60°).
24. 11. Kaiser, E.M.; Woodruff, R.A. J. Org. Chem. 1970, 35, 1198-1199.
25. 2)