The dihydrofuran template approach to furofuran synthesis |
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Authors: | Aldous David J Batsanov Andrei S Yufit Dmitrii S Dalençon Anne J Dutton William M Steel Patrick G |
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Institution: | Sanofi-Aventis Pharma Inc, Bridgewater, New Jersey 08807, USA. |
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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-dioxabicyclo3.3.0]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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