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

ABSTRACT: 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.

SUBMITTER: Ali MTM

PROVIDER: S-EPMC8482504 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature

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

Ali Mohd Tajudin Mohd MTM Husin Zurhana Mat ZM Macabeo Allan Patrick G APG

ACS omega 20210915 38

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. ...[more]

PMID: 34604643

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