Organocatalytic One‐pot Synthesis of Pseudo‐Terpenoids

Structurally elaborate cedrane scaffolds had been synthesized in a really very good yields with higher chemo- and diastereoselectivities in a sequential a single-pot method by utilizing a combination of intermolecular olefination, intramolecular Michael and Michael reactions or intermolecular olefination, intramolecular Michael and aldol reactions as the key methods from the easily accessible hydroxy- p -quinone butanals and phosphoranes beneath the catalytic quantities of quinine at ambient temperature for couple several hours. This is a person of the special 1-pot blend of coupling and annulation routes for the inexperienced synthesis of a library of tricyclic pseudo-terpenoids (cedrane scaffolds) with substantial selectivity and yields. Organocatalytic ring isomerization was highlighted through reworking just one ring into another a single by retro-cyclization. We have discussed completely mechanistic features of these tandem coupling/annulation and ring isomerization reactions dependent on regulate experiments and X-ray crystal structure analysis.

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