Studies towards diarylheptanoid synthesis. Part 1: Synthesis and ring cleavage reactions of hexahydro-2H,5H-pyrano[2,3-b]pyran-2-ones |
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| Authors: | Wei LiKeith T. Mead Laura T. Smith |
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| Affiliation: | Department of Chemistry, Mississippi State University, Mississippi State, MS 39762, USA |
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| Abstract: | Lewis acid promoted anomeric substitution reactions of a stereoselectively prepared hexahydro-2H,5H-pyrano[2,3-b]pyran-2-one derivative was studied as a model for diarylheptanoid synthesis. Aromatic nucleophiles consistently provided the expected thermodynamic C-aryl pyranoside product. |
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| Keywords: | blepharocalyxin diarylheptanoid oxocarbenium ion hexahydro-2H,5H-pyrano[2,3-b]pyran-2-one C-aryl pyranoside |
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