Regenerative γ‑Lactone Annulations: A Modular, Iterative Approach to Oligo-tetrahydrofuran Molecular Stairs and Related Frameworks

A unified, stereocontrolled,
regenerative γ-butyrolactone
annulation approach has been conceptualized and validated through
syntheses of a range of oligo-THFs. The new protocol is short (four
steps), simple (table-top reagents), and efficient (50–61%
overall yields). Although the scope of this approach is unlimited,
it has been demonstrated up to five iterations on commercial γ-butyrolactone
to assemble six fused tetrahydrofuran moieties in a staircase-like
architecture. A selection of exploratory transformations is presented
to exemplify the potential applications of this protocol.