title: Total synthesis of microtubule-stabilizing agent ceratamine A.
abstract: The total synthesis of ceratamine A, a natural microtubule-stabilizing agent with unusual cellular effects, has been accomplished starting from 5-methoxybenzimidazole in 10 steps in an overall yield of 12.7%. The key steps in the synthesis involved the Schmidt rearrangement to construct the azepine ring, the alkylation of lactam to introduce the C-5 benzylic side chain, and the highly economical SNAr reaction to install the C-2 methylamine residue.
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences , Beijing 100050, P. R. China.
authors.forename: Qiguo
authors.initials: Q
authors.lastname: Feng
authors.forename: Lulu
authors.initials: L
authors.lastname: Tao
authors.forename: Zhanzhu
authors.initials: Z
authors.lastname: Liu
mesh_terms: D000818:Animals; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D008870:Microtubules / Q000737:chemistry*; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001381:Azepines; D007093:Imidazoles; C485389:ceratamine A