Achmatowicz approach to the asymmetric synthesis of(+)-and(−)-monanchorin  

作　　者：Yuzhi Ma Rajender Vemula Qi Zhang Bulan Wu George A.O'Doherty 

机构地区：[1]Department of Chemistry and Chemical Biology,Northeastern University,Boston MA 02115,United States [2]Department of Pharmacology and Experimental Therapeutics,Boston University School of Medicine,Boston MA 02118,United States [3]Division of Natural Sciences,College of Natural&Applied Sciences,University of Guam,Mangilao GU 96923,United States

出　　处：《Green Synthesis and Catalysis》2022年第2期156-161,共6页绿色合成与催化（英文）

基　　金：We acknowledge the National Science Foundation(No.CHE-2102649);the National Institutes of Health(Nos.AI142040 and AI154860)for financial support.

摘　　要：The full account of our development of a de novo asymmetric total synthesis of(+)-monanchorin has been reported.The optimized synthesis provided access to either enantiomer of the guanidine alkaloid natural product in nine steps from the commodity chemicals furan and caproic acid.The route relied upon the asymmetric Noyori hydrogen transfer reduction of an achiral acylfuran to introduce the absolute stereochemistry.In addition,an Achmatowicz rearrangement,a diastereoselective palladium-catalyzed glycosylation,a reductive amination and an acid-catalyzed bicyclic guanidine mixed acetal formation were used to complete the synthesis.

关 键 词：Monanchorin Asymmetric synthesis Achmatowicz Pd-glycosylation Reductive amination Guanidine natural product Alkaloid natural product 

分 类 号：O62[理学—有机化学]