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

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journal contribution
posted on 2021-09-15, 17:06 authored by Mohd Tajudin Mohd Ali, Zurhana Mat Husin, Allan Patrick G. Macabeo
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.