Journal article
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 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.
Language: | English |
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Year: | 2001 |
Pages: | 4630-4634 |
ISSN: | 15206904 and 00223263 |
Types: | Journal article |
DOI: | 10.1021/jo0101297 |
ORCIDs: | Madsen, Robert |