title: Highly efficient synthesis of novel methyl 13(2)-methylene mesopyropheophorbide a and its stereoselective Michael addition reaction.
abstract: Treatment of methyl mesopyropheophorbide a with formaldehyde under basic conditions gave a novel 13(2)-methylene derivative in 85% yield; under acidic conditions, the corresponding 20-hydroxymethyl derivative was obtained in 65% yield. The high reactivity of the enone structural motif existed in the former product provides a unique way to construct some novel chlorophyll a derivatives for various applications. Stereoselective Michael reaction of this compound is studied and discussed.
authors.affiliation: College of Chemistry and Chemical Engineering, Yantai University, Yantai, 264005, China. wjj1955@163.com.
authors.forename: Jiazhu
authors.initials: J
authors.lastname: Li
authors.forename: Yang
authors.initials: Y
authors.lastname: Liu
authors.forename: Xi-Sen
authors.initials: XS
authors.lastname: Xu
authors.forename: Yan-Long
authors.initials: YL
authors.lastname: Li
authors.forename: Shan-Guo
authors.initials: SG
authors.lastname: Zhang
authors.forename: Il
authors.initials: I
authors.lastname: Yoon
authors.forename: Young Key
authors.initials: YK
authors.lastname: Shim
authors.forename: Jin-Jun
authors.initials: JJ
authors.lastname: Wang
authors.forename: Jun-Gang
authors.initials: JG
authors.lastname: Yin
mesh_terms: D005557:Formaldehyde / Q000737:chemistry*; D008968:Molecular Conformation; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D011166:Porphyrins; D005557:Formaldehyde