title: Complexity generation by chemical synthesis: a five-step synthesis of (-)-chaetominine from L-tryptophan and its biosynthetic implications.
abstract: We demonstrated, for the first time, that on the basis of chemistry principles, the hexacyclic peptidyl alkaloid (−)-chaetominine (1) can be synthesized in a straightforward manner from L-Trp. The approach features the efficient generation of molecular complexity via a tandem C3/C14 syn-selective epoxidation (dr = 3:2)–annulative ring-opening reaction and a regioselective epimerization at C14. The successful production of (−)-chaetominine (1) from L-Trp could be helpful for revealing how the configuration of L-tryptophan becomes inverted in the biosynthetic pathway of (−)-chaetominine (1).
authors.affiliation: Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China.
authors.forename: Chu-Pei
authors.initials: CP
authors.lastname: Xu
authors.forename: Shi-Peng
authors.initials: SP
authors.lastname: Luo
authors.forename: Ai-E
authors.initials: AE
authors.lastname: Wang
authors.forename: Pei-Qiang
authors.initials: PQ
authors.lastname: Huang
mesh_terms: D053898:Biosynthetic Pathways; D002625:Chemistry, Organic / Q000379:methods*; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000138:chemical synthesis / Q000737:chemistry; D014364:Tryptophan / Q000737:chemistry*
chemical_list: D026121:Indole Alkaloids; D010456:Peptides, Cyclic; C522312:chaetominine; C541864:kapakahine B; C476160:kapakahine F; D014364:Tryptophan