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Improved asymmetric syntheses of (R)-(−)-homocitrate and (2R,3S)-(−)-homoisocitrate, intermediates in the α-aminoadipate pathway of fungi

✍ Scribed by Guoxiang Ma; David R.J Palmer


Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
71 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis


Improved asymmetric syntheses of the title compounds are reported. Both products are produced through diastereoselective alkylation of malic acid; (R)-homocitrate synthesis uses the self-regeneration of stereocenters approach. Both procedures represent an improvement in yield over existing methods without loss of stereoselectivity.


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Asymmetric Syntheses via Heterocyclic In
✍ Schöllkopf, Ulrich ;Bardenhagen, Jürgen 📂 Article 📅 1987 🏛 John Wiley and Sons 🌐 English ⚖ 534 KB

The titanium derivative 4a of the bislactim ether l a from cyclo-(L-Val-Gly) reacts with + m a t u r a t e d aldehydes 5 exclusively by 1.2-addition in a highly diastereowlective mode to give virtually only the (2R,l'S) diastereomers of type 6. Upon hydrolysis these furnish the methyl (2R,3S)-thrm-2