Asymmetric Synthesis of N,O‑Heterobicyclic Octanes and (−)-Geissman–Waiss Lactone

A short, asymmetric synthesis of tetrahydro-2H-furo­[3,2-b]­pyrrole derivatives and (−)-Geissman–Waiss lactone starting from meso-cyclohexadiene epoxide is described. Pivotal transformations in the developed synthetic procedure include asymmetric epoxide ring opening to install the requisite 1S,5S stereocenters and oxidative lactonization/lactamization sequences. This route provides a streamlined synthetic pathway toward necine alkaloids.