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Abstract Attempts to the construction of B/C ring and E ring in melotenine A are described. Based on para-dienone chemistry, a tactical application of tandem aminolysis/aza-Michael addition reaction was made… Click to show full abstract
Abstract Attempts to the construction of B/C ring and E ring in melotenine A are described. Based on para-dienone chemistry, a tactical application of tandem aminolysis/aza-Michael addition reaction was made to access highly functionalized building blocks with the pyrrolo[2,3-d]carbazole tetracyclic unit (A/B/C/D ring). Albeit negative results for assembling the dihydroazepine unit (E ring) by using the proposed fragmentation reaction of gem-dihalocyclopropanes, an alternative strategy based on ring closing metathesis was evolved to forge the E ring possessing a twisted 1,3-diene unit embedded in the rigid skeleton of melotenine A.
Journal Title: Tetrahedron
Year Published: 2019
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