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

Green Synthesis and Catalysis

卷:3

George A. O'Doherty¹  Rajender Vemula²  Yuzhi Ma²  Qi Zhang³  Bulan Wu⁴ 

[1] Applied Sciences, University of Guam, Mangilao GU 96923, United States;

[2] Department of Chemistry and Chemical Biology, Northeastern University, Boston MA 02115, United States;

[3] Department of Pharmacology and Experimental Therapeutics, Boston University School of Medicine, Boston MA 02118, United States;

[4] Division of Natural Sciences, College of Natural &

关键词: Monanchorin;    Asymmetric synthesis;    Achmatowicz;    Pd-glycosylation;    Reductive amination;    Guanidine natural product;   

DOI  :  

来源: DOAJ

【 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.

【 授权许可】

Unknown