Stereoselective synthesis of (2S,3S,4Z)-4-fluoro- 1,3-dihydroxy- 2-(octadecanoylamino)octadec- 4-ene, [(Z)-4-fluoroceramide], and its phase behavior at the air/water interface

• Gergana S. Nikolova and
• Günter Haufe

Beilstein J. Org. Chem. 2008, 4, No. 12, doi:10.3762/bjoc.4.12

• configuration (2S,3S) of the products is controlled by the chiral auxiliary. In recent years several studies on cell membrane lipid models suggested that ceramide could act indirectly as a messenger by modulation of membrane properties. The membrane lipids (mostly sphingomyelin) together with cholesterol are

• networks, because its polar head groups can act both as acceptor and as a donor, ceramide, when added or generated in situ in the membrane, can segregate from the other lipids and cause coalescence of the small lipid raft domains to give highly ordered ceramide-enriched domains. Moreover, due to the small

Transition- metal/Lewis acid free synthesis of acyl benzothiophenes via C-C bond forming reaction

• Sarbani Pal,
• Mohammad Ashrafuddin Khan,
• P. Bindu and
• P. K. Dubey

Beilstein J. Org. Chem. 2007, 3, No. 35, doi:10.1186/1860-5397-3-35

• lipids while displaying potent estrogen antagonist properties in the breast and uterus. A most common example of SERM is tamoxifen which has been the therapy of choice in the endocrine treatment of all stages of hormone-dependent breast cancer and in the primary and secondary chemoprevention of breast