Construction of the septahydroxylated ABC-ring system of dihydro-β-agarofurans: application of 6-exo-dig radical cyclization?
Chemical Communications Pub Date: 2017-03-20 DOI: 10.1039/C7CC00507E
Abstract
A synthetic route to the septahydroxylated ABC-ring system of dihydro-β-agarofurans was established. The B-ring was formed by a base-promoted diastereoselective Diels–Alder reaction between 3-hydroxy-2-pyrone and a D-glyceraldehyde-derived dienophile, while the C-ring was cyclized by PhSeCl-mediated etherification. The remaining A-ring was constructed via a 6-exo-dig radical reaction. Selective transformations gave rise to the ABC-ring system 1 with nine contiguous stereocenters. The thus obtained 1 corresponded to the enantiomer of the densely oxygenated core structure of dihydro-β-agarofurans.
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Journal Name：Chemical Communications
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