Total Synthesis of Bipenicilisorin and Assignment of the Absolute Configuration.

Autor: Fukuda E; Graduate School of Science, Osaka Metropolitan University, 3-3-138 Sugimoto, Sumiyoshi, Osaka 558-8585, Japan., Fujiwara I; Graduate School of Science, Osaka Metropolitan University, 3-3-138 Sugimoto, Sumiyoshi, Osaka 558-8585, Japan., Maruno S; Graduate School of Science, Osaka Metropolitan University, 3-3-138 Sugimoto, Sumiyoshi, Osaka 558-8585, Japan., Motomura K; Graduate School of Science, Osaka Metropolitan University, 3-3-138 Sugimoto, Sumiyoshi, Osaka 558-8585, Japan., Endo S; Graduate School of Science, Osaka Metropolitan University, 3-3-138 Sugimoto, Sumiyoshi, Osaka 558-8585, Japan., Iwasaki A; Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan., Fukuta T; Department of Physical Pharmaceutics, School of Pharmaceutical Sciences, Wakayama Medical University, 25-1 Shichiban-cho, Wakayama 640-8156, Japan., Nakayama A; Graduate School of Science, Osaka Metropolitan University, 3-3-138 Sugimoto, Sumiyoshi, Osaka 558-8585, Japan., Shinada T; Graduate School of Science, Osaka Metropolitan University, 3-3-138 Sugimoto, Sumiyoshi, Osaka 558-8585, Japan.
Jazyk: angličtina
Zdroj: Journal of natural products [J Nat Prod] 2024 May 24; Vol. 87 (5), pp. 1394-1400. Date of Electronic Publication: 2024 May 05.
DOI: 10.1021/acs.jnatprod.4c00114
Abstrakt: 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 .
Databáze: MEDLINE
Externí odkaz: