Abstract
The title compounds have been prepared from previously synthesized 2-endo-acetoxy-3-endohydroxy-7-oxabicyclo[2.2.1]hept-5-ene and 3-acetoxy-4-hydroxy-2,5-divinyl-furan via intramolecular electrophilic cyclization. Both types of compounds constitute new functionalized oxetane ring systems.
Highlights
The oxetane ring system1 constitutes subunits of important naturally occurring compounds such as taxoids,2 thromboxane A2 (TXA2),3 some sesquiterpene lactones,4 diterpenoids5 and mediumsized cyclic ethers.6 On the other hand these compounds are valuable monomers in different polymerization processes7 being well established synthetic intermediates8 and useful tools in drug discovery.9On the other hand, compounds possessing the 4,7-dioxatricyclo[3.2.1.03,6]octane and 2,6dioxabicyclo[3.2.0]heptane skeletons constitute two interesting class of compounds bearing an oxetane subunit
Recently20 we have reported the synthesis of enantiomerically enriched 7-oxanorbornene derivative 10 (Scheme 3) via Diels-Alder cycloaddition between furan and vinylene carbonate followed by hydrolysis and enzymatic desymmetrization
We have described an efficient method for the preparation of 2,8disubstituted-4,7-dioxatricyclo[3.2.1.03,6]octane derivatives starting from readily accessible oxanorbornenic compounds
Summary
The oxetane ring system1 constitutes subunits of important naturally occurring compounds such as taxoids,2 thromboxane A2 (TXA2),3 some sesquiterpene lactones,4 diterpenoids5 and mediumsized cyclic ethers.6 On the other hand these compounds are valuable monomers in different polymerization processes7 being well established synthetic intermediates8 and useful tools in drug discovery.9On the other hand, compounds possessing the 4,7-dioxatricyclo[3.2.1.03,6]octane and 2,6dioxabicyclo[3.2.0]heptane skeletons (structures 1 and 2 respectively, Figure 1) constitute two interesting class of compounds bearing an oxetane subunit. Compound 10 is a suitable starting material for the synthesis of 2,8-disubstituted-4,7-dioxatricyclo[3.2.1.03,6]octane derivatives 12 via intramolecular etherification (endo hydroxyl group at the position 2 of the starting material 10) of the epi-cation intermediate generated by electrophilic addition on the double bond of 10 (Scheme 4a).
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