Synthesis of threo- and erythro-bis(2,2'-tetrahydrofuran). A novel serendipitous synthesis of a spiroketal

Article abstract of DOI:10.1016/S0040-4039(99)00173-2

Racemic threo-bis(2,2'-tetrahydrofuran) and meso-erythro-bis(2,2'- tetrahydrofuran) have been prepared by stereochemically unambiguous routes. Treatment of 2-(1'-bromo-4'-hydroxybutyl)-tetrahydrofuran with base or silver(I) tetrafluoroborate effected cyclisation to 1,6-dioxa- spiro[4.5]decane.