Total Synthesis of Indolizidine Alkaloids via Nickel-Catalyzed (4 + 2) Cyclization

A Ni-catalyzed (4 + 2) cycloaddition of alkynes and azetidinones toward piperidinones was used as key reaction in the enantioselective synthesis of naturally occurring indolizidine alkaloids. The reaction benefits from the use of an easily accessible azetidinone as an advanced and divergent intermed...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2020-02, Vol.22 (3), p.924-928
Main Authors: Renner, Jonas, Thakur, Ashish, Rutz, Philipp M, Cowley, Jacob M, Evangelista, Judah L, Kumar, Puneet, Prater, Matthew B, Stolley, Ryan M, Louie, Janis
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A Ni-catalyzed (4 + 2) cycloaddition of alkynes and azetidinones toward piperidinones was used as key reaction in the enantioselective synthesis of naturally occurring indolizidine alkaloids. The reaction benefits from the use of an easily accessible azetidinone as an advanced and divergent intermediate to build the indolizidine core. This methodology has been applied in the total syntheses of (+)-septicine, (+)-ipalbidine, and (+)-seco-antofine to illustrate the applicability of the general approach.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b04479