Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 3, Pages 771-774Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1qo01578h
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The synthesis of six Stemona alkaloids using racemic Stemomide as a common intermediate was achieved, with thioamides facilitating separation of isosaxorumamide and saxorumamide and promoting the first syntheses of four other alkaloids through chemoselective reduction and oxidation.
Six Stemona alkaloids were synthesized racemically using stemoamide, obtained via a cascade cyclization or our reported transannular cyclization of parvistemoamide, as the common intermediate. Thioamides facilitated the separation of isosaxorumamide and saxorumamide, and promoted the first syntheses of other four N-oxide or pyrrolidine bearing Stemona alkaloids via chemoselective reduction and oxidation.
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