Bioinspired Diversification Approach Toward the Total Synthesis of Lycodine-Type Alkaloids.

ABSTRACT: Nitrogen heterocycles (azacycles) are common structural motifs in numerous pharmaceuticals, agrochemicals, and natural products. Many powerful methods have been developed and continue to be advanced for the selective installation and modification of nitrogen heterocycles through C-H functionalization and C-C cleavage approaches, revealing new strategies for the synthesis of targets containing these structural entities. Here, we report the first total syntheses of the lycodine-type Lycopodium alkaloids casuarinine H, lycoplatyrine B, lycoplatyrine A, and lycopladine F as well as the total synthesis of 8,15-dihydrohuperzine A through bioinspired late-stage diversification of a readily accessible common precursor, N-desmethyl-β-obscurine. Key steps in the syntheses include oxida

SUBMITTER: Haley HMS 

PROVIDER: S-EPMC8017526 | biostudies-literature | 2021 Mar

REPOSITORIES: biostudies-literature