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J Org Chem
; 72(10): 3949-51, 2007 May 11.
Article
in English
| MEDLINE
| ID: mdl-17432907
ABSTRACT
The title compounds were prepared by a straightforward two-step procedure. Tartaric acid was first protected as either a bis(ketal) or a bis(acetal). This intermediate was then treated with potassium tert-butoxide at reduced temperature to effect a stereoselective elimination leading to the Z diastereomer of the alpha,beta-unsaturated acid. This protocol is useful for the laboratory-scale synthesis of these compounds but can also be scaled up to produce kilogram quantities of the material.
Subject(s)
Carboxylic Acids/chemistry , Dioxolanes/chemistry , Dioxolanes/chemical synthesis , Methylation , Molecular Structure , Stereoisomerism
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