Short Formal Syntheses of Lycorine and Congeners Using a 5 -Endo-Trig /6 -Endo-Trig Radical Cyclization Sequence.

Autor: Tan S; Institute for Advanced and Applied Chemical Synthesis, College of Pharmacy, Jinan University, Guangzhou, Guangdong 510632, China.; Laboratoire de Synthèse Organique, CNRS, École Polytechnique, Palaiseau 91128, France., Zard SZ; Laboratoire de Synthèse Organique, CNRS, École Polytechnique, Palaiseau 91128, France., Pham LN; Institute for Nanoscale Science and Technology, College of Science and Engineering, Flinders University, Adelaide, South Australia 5042, Australia., Coote ML; Institute for Nanoscale Science and Technology, College of Science and Engineering, Flinders University, Adelaide, South Australia 5042, Australia., Banwell MG; Institute for Advanced and Applied Chemical Synthesis, College of Pharmacy, Jinan University, Guangzhou, Guangdong 510632, China., Lan P; Institute for Advanced and Applied Chemical Synthesis, College of Pharmacy, Jinan University, Guangzhou, Guangdong 510632, China., White LV; Institute for Advanced and Applied Chemical Synthesis, College of Pharmacy, Jinan University, Guangzhou, Guangdong 510632, China.; Laboratoire de Synthèse Organique, CNRS, École Polytechnique, Palaiseau 91128, France.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2024 May 24; Vol. 26 (20), pp. 4292-4296. Date of Electronic Publication: 2024 May 10.
DOI: 10.1021/acs.orglett.4c01271
Abstrakt: Here, we report a practical route to medicinally interesting lycorine congeners alongside formal syntheses of various lycorine-type natural products, including lycorine itself. The efficiency of our strategy derives from a back-to-back 5 -endo-trig /6 -endo-trig radical cyclization sequence, which we systematically studied both experimentally and computationally. The results of our work will facilitate future development of urgently needed antiviral therapeutics based on lycorine.
Databáze: MEDLINE