title: A facile synthesis of (+/-)-heliannuol-D.
abstract: A facile synthesis of (+/-)-heliannuol-D 1, which serves as an allelopathic chemical in nature and a potential lead compound in the search for new herbicides, has been achieved in a linear 11 steps, together with its epimer. The synthesis commenced with 4-methoxy-3-methyl-acetophenone, through the Baeyer-Villiger reaction, lithiation and addition, epoxidation and intramolecular cyclization to give (+/-)-heliannuol-D (1) and its epimer (la) in 32.6% overall yield. Our synthetic approach is cost-effective; this will be helpful in applying this kind of compound for the development of a new generation of agrochemicals.
authors.affiliation: College of Science, Northwest A&F University, Yangling, Shaanxi Province 712100, PR China.
authors.forename: Tao
authors.initials: T
authors.lastname: Zhang
authors.forename: Liang-Zhu
authors.initials: LZ
authors.lastname: Huang
authors.forename: You-Qiang
authors.initials: YQ
authors.lastname: Li
authors.forename: Yimg-Meng
authors.initials: YM
authors.lastname: Xu
authors.forename: Zhen-Ting
authors.initials: ZT
authors.lastname: Du
mesh_terms: D064089:Allelopathy; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D006368:Helianthus / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis*
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D012717:Sesquiterpenes; C476206:heliannuol D