Efficient synthesis of enantiopure conduritols by ring-closing metathesis

Morten Jørgensen, Erik Høgh Iversen, Andreas Lundtang Paulsen, Robert Madsen

Research output: Contribution to journalJournal articleResearchpeer-review


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 farmer 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.
Original languageEnglish
JournalJournal of organic chemistry
Issue number13
Pages (from-to)4630-4634
Publication statusPublished - 2001


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