Acid-catalysed iterative generation of <i>o</i>-quinone methides for the synthesis of dioxabicyclo[3.3.1]nonanes: total synthesis of myristicyclins A–B
Santosh J. Gharpure, S. Jegadeesan, Dharmendra S. Vishwakarma
Abstract
-QMs/[4+2] cycloaddition/intermolecular Michael addition/cyclative acetalization in a cascade sequence for the synthesis of dioxabicyclo[3.3.1]nonanes. The 'one-pot', controlled cascade sequence successfully provided the shortest route amenable for gram scale synthesis of natural products (±)-myristicyclins A-B.
Topics & Concepts
ChemistrySequence (biology)Total synthesisStereochemistryCascadeBrønsted–Lowry acid–base theoryCombinatorial chemistryOrganic chemistryCatalysisBiochemistryChromatographySynthesis of Indole DerivativesBioactive natural compoundsAlkaloids: synthesis and pharmacology