AI Article Synopsis
- Flash vacuum pyrrolysis of vinyl epoxides results in the efficient production of cis-dihydrofuran carboxylic esters with favorable yields and specific stereos selectivities.
- By using base-promoted epimerization, researchers can create the complementary trans series of these compounds.
- This method facilitates the creation of complex structures like the 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane core found in natural lignans, allowing for controlled production of different stereochemistries.
Article Abstract
Flash vacuum pyrrolysis of vinyl epoxides provides cis-dihydrofuran carboxylic esters in good yields and diastereoselectivities, which, on base-promoted epimerisation afford the complementary trans series. The compounds provide a viable template for a Lewis acid promoted cyclisation to provide the 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane core found in the furofuran series of natural lignans. This strategy is stereodivergent and can be controlled to provide the exo-exo, exo-endo or endo-endo stereochemistries. The approach has been exemplified in syntheses of the sesamyl furofurans (+/-)-epiasarinin and (+/-)-asarinin.
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| http://dx.doi.org/10.1039/b604952d | DOI Listing |
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