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Enantioselective synthesis of α-hydroxylated enterolactone and analogs

✍ Scribed by Michael Sefkow; Alexandra Kelling; Uwe Schilde

Book ID
104230970
Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
90 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

A short and general synthesis of enantiomerically pure a-hydroxylated lactone lignans starting from commercially available i Pr malate is presented. Key reactions are two stereoselective alkylations of malic acid derivatives. Some enhancements of the alkylation of malic acid esters and a general extension of the alkylation of dioxolanones is reported. Proof of the stereochemical outcome of the alkylation reactions is provided by X-ray diffraction analysis of a-hydroxy-a,b-dibenzyl-g-butyrolactone, the first crystal structure of an enantiomerically pure a-hydroxylated lactone lignan.

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Crystal and molecular structure of 1α-hy
Crystal and molecular structure of 1α-hydroxylated analogs of vitamins D
✍ Waclaw Kolodziejski; Krzysztof Woźniak; Joanna Herold; Paulina M. Dominiak; Andr 📂 Article 📅 2005 🏛 Elsevier Science 🌐 English ⚖ 351 KB

Structures of two 1a-hydroxylated analogs of vitamins D, 1a-hydroxycholecalciferol and 1a-hydroxyergocalciferol, were solved and refined using single crystal X-ray diffraction. Crystallographic results are verified by 13 C CP/MAS NMR. This method provided also information on molecular mobility of an