title: Total synthesis of (-)-indolactam V.
abstract: The total synthesis of protein kinase C activator (-)-indolactam V (IL-V) has been successfully completed with two separate approaches: From known 4-nitrotryptophan derivative 3 in 8 steps (49% overall yield) and from L-glutamic acid in 12 steps (18% overall yield), where 4-nitrotryptophanol derivative 4 served as a key intermediate. Derivatives 3 and 4, both incorporating indole 4-substitution and the C-9 stereocenter in IL-V, were synthesized via the Pd-catalyzed indole synthesis from 3-nitro-2-iodoaniline 5 with aldehydes 6 and 7, respectively. Aldehyde 7 was, meanwhile, synthesized from l-glutamic acid in 5 steps (68% yield). Lactamization of the 9-membered ring was achieved using HATU in THF in good yield.
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 38 Xueyuan Road, Beijing, 100191, China.
authors.forename: Zhengren
authors.initials: Z
authors.lastname: Xu
authors.forename: Fengying
authors.initials: F
authors.lastname: Zhang
authors.forename: Lihe
authors.initials: L
authors.lastname: Zhang
authors.forename: Yanxing
authors.initials: Y
authors.lastname: Jia
mesh_terms: D007211:Indoles / Q000138:chemical synthesis*; D007769:Lactams / Q000138:chemical synthesis*; D015394:Molecular Structure
chemical_list: D007211:Indoles; D007769:Lactams; C043969:indolactam V