A Comprehensive Approach to C3a-Aryl-Substituted Hydroindole Alkaloids by Utilizing Enantioselective Gold Catalysis

Jhen Kuei Yu; Constantin Czekelius

doi:10.1055/s-0043-1775389

Synthesis, Table of Contents

Synthesis 2024; 56(20): 3147-3159
DOI: 10.1055/s-0043-1775389

paper

Special Topic Dedicated to Prof. Erick Carreira

A Comprehensive Approach to C3a-Aryl-Substituted Hydroindole Alkaloids by Utilizing Enantioselective Gold Catalysis

Jhen Kuei Yu

,

Constantin Czekelius ∗

Abstract

All articles of this category

Dedicated to Prof. Erick M. Carreira on the occasion of his 60^th birthday

Abstract

A diversity-oriented total synthesis for Amaryllidaceae alkaloids incorporating the frequently found C3a-arylated hydroindole moiety was developed. Chiral-anion-induced gold(I) catalysis was employed for the cyclization of 1,4-diynes to the pyrrolidine and the installation of the all-carbon quaternary stereocenter. Both enantiomeric series of crinine-type alkaloids in high enantiopurity were accessible by this methodology. The formal synthesis of a wide range of Amaryllidaceae alkaloids is described, such as (+)-vitattine, (–)-epi-vitattine, (–)-elwesein, (–)-epi-elwesein, (–)-crinine, (–)-epi-crinine, (–)-buphanisine, (–)-flexinine, and (+)-gracilamine.

Key words

alkaloids - enantioselectivity - gold catalysis - desymmetrization - quaternary centers

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References

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