Studies towards the total synthesis of condylacarpine and studies towards the enantioselective synthesis of (+)-methyl lysergate
Abstract
An iminium ion cascade sequence was designed and its implementation attempted
to form the pentacyclic core structure of the natural product condylocarpine. Trapping of
the transient Pictet-Spengler-type spiroindolenium ion with a latent nucleophile would
form two of the five rings of condylocarpine in a regioselective manner.
Progress towards the first fully stereocontrolled synthesis of a lysergic acid
derivative has been described. The route utilizes intermediates with the appropriate
oxidation state for the target, and the two stereocenters are installed via asymmetric
catalysis. The d ring and second stereocenter were simultaneously formed via an
unprecedented microwave heated asymmetric ring closing metathesis (ARCM).
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