Synthesis of norbornanepentols: analogues of inositols.
The synthesis of endo-5,6-exo-2,3-syn-7-norbornanepentol (5), endo-5-exo-2,3,6-syn-7-norbornanepentol (14), and 7-exo-2,3,5,6-norbornanepentol (16) are described. cis-Hydroxylation of 7-tert-butoxynorbornadiene (1) gave the exo-diol 2, endo-diol 3, and tetrol 4. The latter was deprotected to give pentol 5. Oxidation of alkene 6 afforded diacid 7 and two minor products: the exo-diol 8 and alpha-hydroxyketone 9. cis-Hydroxylation of 6 gave the endo- and exo-diols 10 and 8. Acetalation of 8 furnished the bis(dioxolane) 11. Reduction of ketone 9 gave the trans-diol 12. Deblocking of 8 and 12 led the tetrol 15 or pentols 16 and 14. The structure of tetrol 4 was confirmed by X-ray diffraction. Compounds 4, 5 and 16 were devoid of antitumor or antiviral activity.
Ben Cheikh
A
A
Department of Chemistry, Michigan Cancer Foundation, Detroit.
Craine
L E
LE
Zemlicka
J
J
Hegg
M J
MJ
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D055598:Chemical Phenomena; D002621:Chemistry; D007294:Inositol / Q000031:analogs & derivatives*; D008969:Molecular Sequence Data; D009636:Norbornanes; D014961:X-Ray Diffraction
D009636:Norbornanes; C064838:2,3,5,6,7-norbornanepentol; D007294:Inositol