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

Abstract

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
Volume66
Issue number13
Pages (from-to)4630-4634
ISSN0022-3263
Publication statusPublished - 2001

Fingerprint Dive into the research topics of 'Efficient synthesis of enantiopure conduritols by ring-closing metathesis'. Together they form a unique fingerprint.

Cite this