Total Synthesis of Indolizidine Alkaloids via Nickel-Catalyzed (4 + 2) Cyclization
Jonas Renner1, Ashish Thakur1, Philipp M Rutz1
1Department of Chemistry , University of Utah , 315 South 1400 East , Salt Lake City , Utah 84112-8450 , United States.
Abstract:
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.
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