Towards the total synthesis of Daphniyunnine B

  • John Ward

Student thesis: Phd


This thesis describes the development of a series of synthetic routes towards the first synthesis of Daphniyunnine B, a Daphniphyllum alkaloid, utilising novel reactions and cascades. Studies began with an envisaged enantioselective Michael cascade reaction, which alternatively gave rise to a novel, efficient Michael-aldol cascade reaction affording perhydroindole structures in moderate to excellent diastereoselectivity.The enantioselective synthesis of the methyl-substituted core of Daphniyunnine B was achieved via an initial highly enantioselective organocatalytic Michael addition followed by a stereoselective organocatalytic intramolecular Michael addition.The stereocontrolled synthesis of the AC bicyclic core of (±) Daphniyunnine B was achieved via a quaternisation cyclisation approach.The stereocontrolled synthesis of the ACD tricyclic core of (±) Daphniyunnine B was achieved via an intramolecular Diels-Alder fragmentation reaction. Preliminary studies of an enantioselective variant are encouraging.
Date of Award1 Aug 2011
Original languageEnglish
Awarding Institution
  • The University of Manchester
SupervisorDavid Procter (Supervisor)

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