Dihydro- and Tetrahydrofuran Building Blocks from 1,4:3,6-Dianhydromannitol. 1. Synthesis of (1S,5R,7R)-endo-(-)- and (1S,5R,7S)-(-)-exo-Brevicomin and (R)-(+)-Dodecanolide

Article abstract of DOI:10.1021/jo00069a015

The eliminative ring fission of iodides derived from 1,4:3,6-dianhydromannitol has been exploited for preparing three enantiomerically pure species, 1-3, which feature a di- or tetrahydrofuran moiety and one or two stereogenic centers.These species are extremely versatile building blocks for the construction of natural products.Their potential was demonstrated by the synthesis of the title insect pheromones.