Efficient synthesis of enantiopure conduritols by ring-closing metathesis.
Two short synthetic approaches to enantiopure conduritols are described starting from the chiral pool. In both cases, the cyclohexene ring is assembled via ring-closing olefin metathesis. The terminal diene precursers for the metathesis reaction are prepared either from octitols or from tartaric acids. The former route involves a new method for selective bromination of the primary positions in long-chain carbohydrate polyols. Subsequent reductive elimination with zinc then generates the diene. The latter route uses a highly diastereoselective addition of divinylzinc to tartaric dialdehydes for preparation of the dienes.
Jørgensen
M
M
Department of Organic Chemistry, Technical University of Denmark, DK-2800 Lyngby, Denmark.
Iversen
E H
EH
Paulsen
A L
AL
Madsen
R
R
D000475:Alkenes / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry; D003511:Cyclohexanols / Q000138:chemical synthesis* / Q000737:chemistry; D053138:Cyclohexenes; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D013644:Tartrates / Q000737:chemistry
D000475:Alkenes; D002241:Carbohydrates; D003511:Cyclohexanols; D053138:Cyclohexenes; D004791:Enzyme Inhibitors; D013644:Tartrates; C090988:conduritol B; C029768:tartaric acid