Collect. Czech. Chem. Commun. 1997, 62, 1089-1094

Synthesis of 2α,3α-Epoxy-9β-benzoyloxy-β-agarofuran and 2,3-Dehydro-4β,12-epoxy-9β-benzoyloxy-β-dihydroagarofuran

Fajun Nana, Lijun Liua, Zhaoming Xionga, Yonggang Chena, Tongshuang Lib and Yulin lia

a National Laboratory of Applied Organic Chemistry and Institute of Organic Chemistry, Lanzhou University, Lanzhou 730 000, People's Republic of China
b Department of Chemistry, Hebei University, Baoding 071 002, People's Republic of China


The first stereoselective synthesis of 2α,3α-epoxy-9β-benzoyloxy-β-agarofuran (3) and 2,3-dehydro-4β,12-epoxy-9β-benzoyloxy-β-dihydroagarofuran (4) from (-)-carvone in 13 steps, respectively, has been described. In addition, the synthesis of 2,3-dehydro-4β,9β-dihydroxy-β-dihydroagarofuran (13) has also been reported. By the reduction of 4 to give 13, the 4β,12-epoxy configuration of 4 was established.

Keywords: 2α,3α-Epoxy-9β-benzoyloxy-β-agarofuran; 2,3-Dehydro-4β,12-epoxy-9β-benzoyloxy-β-dihydroagarofuran; 2,3-Dehydro-4β,9β-dihydroxy-β-dihydroagarofuran.