Enantioselective Synthesis of (3S,4S)-4-Methyl-3-heptanol, a Beetle Pheromone, via the Regioselective Cleavage of an α-Epoxy Oxazolidine

Synlett

Volumn 1996, Issue 6, 1996, Pages 511-512

  Agami, C ^a   Couty, F ^a   Venier, O ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001918034     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5478     Document Type: Article

References (17)

1. Mori, K. In The Total Synthesis of Natural Products; ApSimon J., Ed.; Wiley, New York, 1992; p. 101.
2. Agami, C.; Couty, F.; Venier, O. Synlett, 1995, 1027.
3. Tripathy, P.B.; Matteson, D.S. Synthesis 1990, 200.
4. 4: C, 66.86; H, 7.59; N, 4.59. Found: C, 66.86; H, 7.63; N, 4.66.
5. 4: C, 67.26; H, 8.47; N, 4.36. Found: C, 67.40; H, 8.47; N, 4.31.
6. Bertz, S.H.; Dabbagh, G.; Villacorta, G.M. J. Am. Chem. Soc. 1982, 104, 5824.
7. Colombo, L.; Gennari, C.: Poli, G.; Scolastico, C. Tetrahedron. Lett., 1985, 26, 5459.
8. 2Br, DMF) afforded bicyclic urethane 9. (Matrix Presented)
9. Hoffmann, R.W., Ladner, W.; Helbig, W. Liebigs Ann. Chem. 1984, 1170.
10. D +11.8 (c, 1.8, hexane)).
11. Isolation of compounds 8a, b, 1 and 4 required great care because they are highly volatile.
12. Mori, K.; Iwasawa, H. Tetrahedron, 1980, 36, 2209.
13. Nagakawa, N.; Mori, K. Agric. Biol. Chem. 1984, 48, 250.
14. Behrens, C.H.; Sharpless, K.B. Aldrichimica Acta, 1983, 16, 67.
15. Fourneau, J.P.; Chantalou, S. Bull. Soc. Chim. Fr. 1945, 12, 845.
16. Bernardi, A.; Cardani, S.; Scolastico, C.; Villa, R. Tetrahedron, 1990, 46, 1987.
17. The possible occurrence of this electrostatic repulsive effect has been suggested to us by Dr. S.G. Davies (Oxford).