AI Article Synopsis
- A novel method for carbocyclization using a carbohydrate-derived lactone acetal from methyl α-d-glucopyranoside has been developed, yielding a highly substituted carbocyclic product as a single stereoisomer.
- The addition of N,N,N',N'-tetramethylethylenediamine significantly increases the reaction yield, and optimized conditions have been extended to other lactone acetals from different carbohydrates.
- Scalability of the reaction has been demonstrated, producing up to 15 grams, and further derivatization has been achieved, including the creation of a rare trans-bicyclo[4.3.0]nonene scaffold, with all structures confirmed by X-ray crystallography.
Article Abstract
A novel Ferrier-type carbocyclization is reported. It involves a carbohydrate-derived lactone acetal synthesized from methyl α-d-glucopyranoside, which upon treatment with excess vinylmagnesium bromide provides a highly substituted carbocyclic product as a single stereoisomer. The yield is greatly increased when N,N,N',N'-tetramethylethylenediamine is added to the reaction mixture. Optimized reaction conditions have been applied to lactone acetals derived from other carbohydrates. Based on the obtained results, a possible reaction mechanism has been proposed. Furthermore, scalability of the reaction up to 15 g scale and derivatization of the carbocyclic product has been demonstrated, including the formation of a rare trans-bicyclo[4.3.0]nonene scaffold via a ring-closing metathesis. The structure of this and all carbocyclic products were confirmed by X-ray crystallographic analysis.
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| http://dx.doi.org/10.1021/acs.joc.7b03079 | DOI Listing |
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