title: Total synthesis of (+/-)-4-demethylenglerin A.
abstract: Racemic 4-demethylenglerin A (1'), a simplified analog of the guaiane-type sesquiterpene englerin A (1), has been synthesized. The cyclic hydrocarbon core structure was built through modified Metz approach using epoxynitrile cyclization and direct Aldol reaction to prepare the precursor of RCM. The primary cytotoxicity test summarized that C4 methyl has marked impacts on the bioactivity.
authors.affiliation: a State Key Laboratory of Bioactive Substance and Function of Natural Medicine, Beijing Key Laboratory of Active Substance Discovery and Druggability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College , Beijing 100050 , China.
authors.forename: Liang
authors.initials: L
authors.lastname: Dong
authors.forename: Xiao-Zhen
authors.initials: XZ
authors.lastname: Jiao
authors.forename: Xiao-Yu
authors.initials: XY
authors.lastname: Liu
authors.forename: Cheng-Sen
authors.initials: CS
authors.lastname: Tian
authors.forename: Xiao-Yu
authors.initials: XY
authors.lastname: Li
authors.forename: Yang-Yang
authors.initials: YY
authors.lastname: Yao
authors.forename: Ping
authors.initials: P
authors.lastname: Xie
mesh_terms: D003500:Cyclization; D006801:Humans; D015394:Molecular Structure; D029803:Phyllanthus / Q000737:chemistry; D045789:Sesquiterpenes, Guaiane / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: C000591877:4-demethylenglerin A; D045789:Sesquiterpenes, Guaiane; C534971:englerin A
keywords: 4-demethylenglerin A; epoxynitrile cyclization; total synthesis