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Updated: Sep 24, 2025

High-throughput Synthesis of Carbohydrates and Functionalization of Polyanhydride Nanoparticles
Published on: July 6, 2012
Gram-scale carbasugar synthesis via intramolecular seleno-Michael/aldol reaction
Piotr Banachowicz1, Szymon Buda1
1Faculty of Chemistry, Jagiellonian University Gronostajowa 2 30-387 Krakow Poland szym.buda@gmail.com.
Abstract:
Carbasugars represent an important category of natural products possessing a broad spectrum of biological activities. Lots of effort has been done to develop gram scale synthesis. We are presenting a new approach to gram scale synthesis of the carbasugar skeleton via intramolecular seleno-Michael/aldol reaction. The proposed strategy gave gram amounts of 6-hydroxy shikimic ester in a tandem process in 36% overall yield starting from d-lyxose. We have attempted to demonstrate the synthetic utility of 6-hydroxyshikimic acid derivatives by covering the important synthetic modifications and related applications, namely synthesis of protected (-)-gabosine E, (-)-MK7606, (-)-valienamine and finally unprotected methyl (-)-shikimate.
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