On the Formation and Transformation of alpha-Iminonitriles, the Desymmetrization of Bicyclic Bislactones and Total Synthesis of (-)-Leucomidine B and (-)-Rhazinilam

Two principle topics are covered in this thesis. The first section deals with the development of novel synthetically useful multicomponent reactions. The development of three multicomponent reactions, based on α-iminonitriles, is presented. The first describes a process for the easy and straightforward synthesis of amides from amines, aldehydes and TMSCN via α-iminonitriles intermediates. The second describes the formation of β-functionalized amides from aldehydes, amines and thiols with again α-iminonitriles as key intermediate structure. The third reaction described covers the formation of α-iminonitriles via a selective oxidative multicomponent process using Oxone and a phase transfer agent. The second section covers the desymmetrization of dimethyl 4,4-disubstituted pimelate fragments via the ring opening of bicyclic bislactones for the formation of optically active ten carbon synthons containing an all carbon quaternary center. These fragments are subsequently used in the total synthesis of three diverse indole alkaloid Leucomidine B. Rhazinilam, Rhazinicine.

Zhu, Jieping
Lausanne, EPFL
Other identifiers:
urn: urn:nbn:ch:bel-epfl-thesis6489-5

Note: The status of this file is: EPFL only

 Record created 2014-12-09, last modified 2018-01-28

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