Synthesis of tetrahydropyranyl diarylheptanoids from Dioscorea villosa
Concise syntheses of four tetrahydropyranyl diarylheptanoids isolated from Dioscorea villosa have been described. The key features include Prins cyclization to construct the tetrahydropyran cores, Keck asymmetric allylation, and Mitsunobu inversion. Optimization of the Prins cyclization conditions in order to minimize racemization has been described. Our syntheses also confirmed the absolute stereochemistry of the natural products.
Synthesis of a novel diarylheptanoid isolated from Zingiber officinale
Syntheses of 4-acetoxy-2,6-disubstituted tetrahydropyrans via Prins cyclisation of homoallylic alcohols with benzylic aldehydes are described and the methodology is applied in the total synthesis of diarylheptanoid 1 confirming both the structure and abso
Parker, Gregory D.,Seden, Peter T.,Willis, Christine L.
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p. 3686 - 3689
(2009/10/04)
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