Relative and absolute configuration of the 3,12-dihydroxypalmitic acids

Liebigs Annales

Volumn , Issue 12, 1996, Pages 2123-2129

  Jakob, Barbara ^a   Gerlach, Hans ^a  

^a UNIVERSITY OF BAYREUTH   (Germany)

Author keywords

3,12 Dihydroxyhexadecanoic acids; Absolute configurations; Ipomea operculata M.; Operculinic acid

Indexed keywords

EID: 33748986699     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199619961226     Document Type: Article

References (17)

1. H. Wagner, P. Kazmaier, Tetrahedron Lett. 1971, 12, 3233-3236.
2. G. Wagner, P. Kazmaier, Phytochemistry 1977, 16, 711-714.
3. E. Graf, H. Bühle, Arch. Pharm. (Weinheim, Germ.) 1974, 307, 628-635.
4. E. Graf, H. Bühle, Arch. Pharm. (Weinheim, Germ.) 1974, 307, 636-643.
5. E. Votocek, V. Prelog, Collect. Czech. Chem. Commun. 1929, 1, 55-64.
6. By repeating the synthesis in ref.[3] we found that an equimolar mixture of erythro-(±)- and threo-(±)-methyl 3,12-dihydroxyhexadecanoate has m.p. 57.5-59.0°C.
7. Jalapinolic acid isolated from related resin glycosides has been shown to be (S)-(+)-11-hydroxyhexadecanoic acid by an enantioselective synthesis: M. Shibuya, K. Kawashima, N. Baek, N. Narita, M. Yoshikawa, I. Kitagawa, Chem. Pharm. Bull. 1989, 37, 1131-1133.
8. B. Küchler, G. Voss, H. Gerlach, Liebigs Ann. Chem. 1991, 545-552.
9. G. Voss, H. Gerlach, Liebigs Ann. Chem. 1982, 1466-1477.
10. G. Voss, H. Gerlach, Helv. Chim. Acta 1983, 66, 2294-2307.
11. A. Thalmann, K. Oertle, H. Gerlach, Org. Synth. 1990, Coll. Vol. 7, 470-472.
12. H. J. Collot, Bull. Soc. Chim. Fr. 1974, 1492-1496.
13. Ch. Liu, J. K. Coward, J. Org. Chem. 1991, 56, 2262-2266.
14. P. H. J. Carlsen, T. Katshuki, V. S. Martin, K. B. Sharpless, J. Org. Chem. 1981, 46, 3936-3938.
15. R. Zelinski, H. Eichel, J. Org. Chem. 1958, 23, 462-465.
16. B. Haase, M. P. Schneider, Tetrahedron: Asymmetry 1993, 4, 1017-1026.
17. Resina jalapae e tubere levi pulv. DAB VI from roots of Brazilian Ipomea operculata (Caesar & Loretz, Hilden).