Asymmetric Synthesis of the Indoloquinolizine Alkaloid (+)‐Cuscutamine via a Diastereoselective Intramolecular Pictet‐Spengler Reaction

A concise total synthesis of Cuscutamine was achieved involving a diastereoselective intramolecular acyl iminium ion mediated Pictet‐Spengler reaction. This synthetic strategy provided a direct route to (11S, 13R)‐Cuscutamine (2) in only 3 steps with an overall yield of 56 % and an enantiomeric rati...

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Bibliographic Details
Published in:European journal of organic chemistry 2024-11, Vol.27 (41)
Main Authors: Max St Pierre, McNulty, James
Format: Article
Language:English
Subjects:
Chemical synthesis
Stereoselectivity
Online Access:Get full text
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Summary:A concise total synthesis of Cuscutamine was achieved involving a diastereoselective intramolecular acyl iminium ion mediated Pictet‐Spengler reaction. This synthetic strategy provided a direct route to (11S, 13R)‐Cuscutamine (2) in only 3 steps with an overall yield of 56 % and an enantiomeric ratio of 88 %. The diastereoselectivity of the reaction is consistent with previous studies that proceed via more highly puckered transition states and the present results thus reveal the importance of the steric contributions to the observed diastereoselectivity.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202400708