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Enantioselective synthesis of the α,α-dimethyl-β-hydroxy : Acid subunit of the oxazolomycin antibiotics

✍ Scribed by Andrew S. Kende; Kuniaki Kawamura; Michael J. Orwat

Book ID: 104244595
Publisher: Elsevier Science
Year: 1989
Tongue: French
Weight: 330 KB
Volume: 30
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)93480-x

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✦ Synopsis

Reaction of the Sn(Il) enolate, generated by the action of SnClz-LiAlH4 on oxazolidinone 5, with benzaldehyde or conjugated Z-enal 8 yields respectively oxaxinedione 6 or 9 with not less than 97 : 3 diastereoselectivity.

Removal of the chiral auxiliary from 9 produces a homochiral model of the CI'CS subunit of the oxarolomycin antibiotics.

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