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Total Synthesis of Bipenicilisorin and Assignment of the Absolute Configuration.

Eigo FukudaIbuki FujiwaraShoki MarunoKaiki MotomuraSeiya EndoArihiro IwasakiTatsuya FukutaAtsushi NakayamaTetsuro Shinada
Published in: Journal of natural products (2024)
The first total synthesis of bipenicilisorin ( 1 ) isolated from Penicillium chrysogenum SCSIO 41001 via its monomer natural product, penicilisorin ( 2 ), was achieved. Penicilisorin was synthesized in four steps from a o -bromobenzaldehyde derivative via the Pd-catalyzed one-pot fluorocarbonylation/lactonization/β-elimination cascade reaction. Iodination of penicilisorin gave 7-iodopenicilisorin which was dimerized by Pd-catalyzed homodimerization to provide (±)-bipenicilisorin. The unknown absolute configuration of naturally occurring (+)-bipenicilisorin was examined by optical resolution of the (±)-synthetic bipenicilisorin and a comparison of experimental and theoretical electronic circular dichroism (ECD) spectra. These results support the absolute configuration of the natural product to be S a . A cytotoxic activity test of (+)-and (-)-bipenicilisorin using A549 cells revealed that (+)- 1 has a lower IC 50 value than (-)- 1 .
Keyphrases
  • induced apoptosis
  • room temperature
  • cell cycle arrest
  • high resolution
  • density functional theory
  • oxidative stress
  • mass spectrometry
  • water soluble