Nonenzymic polycyclization of analogues of oxidosqualene with a preformed C-ring.
Some nonenzymic epoxide-initiated polyolefin cyclization are reported. The presented molecules are partially constrained analogues of (3S)-oxidosqualene, the natural substrate to many important cyclase enzymes. These model compounds feature a preformed C-ring with built-in stereochemical information. The experimental results allow for an instructive comparison with the enzymic processes, particularly those of the cyclases in steroid biosynthesis (i.e. lanosterol synthase).
Winne
Johan M
JM
Ghent University, Department of Organic Chemistry, Krijgslaan 281 (S4), B-9000 Gent, Belgium.
De Clercq
Pierre J
PJ
Milanesio
Marco
M
Pattison
Philip
P
Viterbo
Davide
D
D003500:Cyclization; D008958:Models, Molecular; D008968:Molecular Conformation; D013185:Squalene / Q000031:analogs & derivatives* / Q000737:chemistry
C520393:oxidosqualene; D013185:Squalene