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Issue 29, 2017
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Construction of the septahydroxylated ABC-ring system of dihydro-β-agarofurans: application of 6-exo-dig radical cyclization

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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.

Graphical abstract: Construction of the septahydroxylated ABC-ring system of dihydro-β-agarofurans: application of 6-exo-dig radical cyclization

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Publication details

The article was received on 19 Jan 2017, accepted on 20 Mar 2017 and first published on 20 Mar 2017


Article type: Communication
DOI: 10.1039/C7CC00507E
Citation: Chem. Commun., 2017,53, 4073-4076
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    Construction of the septahydroxylated ABC-ring system of dihydro-β-agarofurans: application of 6-exo-dig radical cyclization

    H. Fujisawa, T. Ishiyama, D. Urabe and M. Inoue, Chem. Commun., 2017, 53, 4073
    DOI: 10.1039/C7CC00507E

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