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ChemInform Abstract: Stereochemical Change in the Lewis Acid-Promoted Reaction of 2-Siloxypyrrole Derived from (L)-Glutamic Acid. Synthesis of a Lactacystin Analogue.

✍ Scribed by H. UNO; N. MIZOBE; Y. YAMAOKA; N. ONO

Publisher: John Wiley and Sons
Year: 2010
Weight: 37 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199831213

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✦ Synopsis

Stereochemical Change in the Lewis Acid-Promoted Reaction of 2-Siloxypyrrole Derived from (L)-Glutamic Acid. Synthesis of a Lactacystin Analogue.

-The enantiopure pyrrolooxazole (I) react with aliphatic aldehydes [cf. (II)] stereoselectively to yield either the isomers (IV) or (VIII) as major products depending on the Lewis acid used. The similar reaction with aromatic aldehydes such as (X) affords the isomer (XII) predominantly irrespective of the Lewis acid. (XII) is transformed to the analogue (XIV) of lactacystin. -(UNO, H.; MIZOBE, N.; YAMAOKA, Y.;

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