The phenomenon of angucyclinones resulting from angucycline C-ring fragmentation is analyzed in terms of generality, biosynthetic origin and plausible function.
A synthetic approach towards rearranged angucyclinones related to Elmenols A and B and their synthetic derivatives has been developed. Carbon skeleton is constructed in a straightforward manner by directed o‐lithiation of m‐anisaldehyde dimethyl acetal and its further nucleophilic addition to properly substituted naphthalene carbaldehydes. The latter can be achieved via several alternative synthetic schemes, the most efficient of them are discussed herein.
This review critically summarized the synthesis of hasubanan alkaloids with the focus on construction of hasubanan core. Historical and recent reports are systemized based on the strategic bonds formation and are given in comparison. Special accents are made on the achievements in collective syntheses, asymmetric syntheses, and biomimetic approaches. Based on the summarized data potential perspectives are highlighted.
Directly accessible 8-substituted tetrahydroquinolines undergo 1,5-hydride shift-triggered cyclization to provide hardly accessible julolidine derivatives in 20-98% yield under scandium (III) triflate catalysis. The scope of the reaction, several follow-up transformations and a remarkable side-process discovered during the conditions optimization are highlighted.
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