Modified Julia-Kocienski Reagents for a Stereoselective Introduction of Trisubstituted Double Bonds: A Formal Total Synthesis of Limazepine E and Barmumycin.

Autor: Sakaine G; Latvian Institute of Organic Synthesis , Aizkraukles 21 , Riga LV-1006 , Latvia., Smits G; Latvian Institute of Organic Synthesis , Aizkraukles 21 , Riga LV-1006 , Latvia.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2018 May 04; Vol. 83 (9), pp. 5323-5330. Date of Electronic Publication: 2018 Apr 18.
DOI: 10.1021/acs.joc.8b00643
Abstrakt: A formal total synthesis of pyrrolo[1,4]benzodiazepine anticancer antibiotic family member limazepine E is described. The synthesis features a stereoselective introduction of a trisubstituted double bond using novel sterically demanding Julia-Kocienski reagents, allowing the number of linear steps to be significantly reduced. The potential of the newly developed reagents has also been demonstrated by the formal total synthesis of barmumycin.
Databáze: MEDLINE