kapakahine-f has been researched along with chaetominine* in 2 studies
2 other study(ies) available for kapakahine-f and chaetominine
| Article | Year |
|---|---|
Double annulative cascade of tryptophan-containing peptides triggered by selectfluor.
A common dearomative strategy toward the kapakahines B/F and chaetominine natural products is reported. The proposed biomimetic strategy generates the tetracyclic α-carboline core in a single step, featuring a selectfluor-mediated dearomatization of preactivated N-Phth-Trp-Xaa-OR dipeptides at the C-terminus. The pivotal cascade includes a double annulation and the formation of three carbon-heteroatom bonds while gaining, for the first time, some insight on the diastereoselectivity outcome during the formation of the α-carboline fragment. Topics: Biological Products; Diazonium Compounds; Indole Alkaloids; Molecular Conformation; Oligopeptides; Peptides, Cyclic; Stereoisomerism; Tryptophan | 2014 |
Complexity generation by chemical synthesis: a five-step synthesis of (-)-chaetominine from L-tryptophan and its biosynthetic implications.
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). Topics: Biosynthetic Pathways; Chemistry, Organic; Indole Alkaloids; Peptides, Cyclic; Tryptophan | 2014 |