Oligo(tetrahydrofurans) (oligo-THFs) 8-12 have been synthesised stereo
selectively. Multiple Williamson reactions were used as key steps. Whi
le oligo-TWFs with an even number of THF rings like the bi-THFs 8 and
9 as well as the tetra-THFs 10 and 11 were obtained by a bidirectional
strategy, the penta-THF 12 with an odd number of THF rings was prepar
ed by a convergent strategy with a sulfone-aldehyde coupling as connec
ting step, The oligo-THF products are important structural features of
natural (Annonaceae acetogenins) and non-natural (artificial inn chan
nels) products.