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A short, asymmetric synthesis of tetrahydro-2 H -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 1 S ,5 S stereocenters and oxidative lactonization/lactamization sequences. This route provides a streamlined synthetic pathway toward necine alkaloids.

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