Application of the B-alkyl suzuki-miyaura cross-coupling reaction to the stereoselective synthesis of analogues of (3S)-oxidosqualene.
[reaction: see text] A general method is described for the direct and stereoselective synthesis of epoxypolyenes via Suzuki-Miyaura cross-coupling reaction of 1-iodoalkenes with B-alkylboron compounds. It allows for the straightforward and convergent assembly of compounds that are structurally similar to (3S)-oxidosqualene, an important intermediate in steroid biosynthesis.
Winne
Johan M
JM
Department of Organic Chemistry, Ghent University, Krijgslaan 281/S4, B-9000 Ghent, Belgium.
Guang
Bing
B
D'Herde
Jo
J
De Clercq
Pierre J
PJ
D002384:Catalysis; D015394:Molecular Structure; D013185:Squalene / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
C520393:oxidosqualene; D013185:Squalene