1558046-41-5Relevant academic research and scientific papers
Bio-inspired step-economical, redox-economical and protecting-group-free enantioselective total syntheses of (-)-chaetominine and analogues
Luo, Shi-Peng,Peng, Qi-Long,Xu, Chu-Pei,Wang, Ai-E,Huang, Pei-Qiang
, p. 757 - 770 (2014)
Full details of the enantioselective four-step and five-step total syntheses of (-)-chaetominine from D-Trp and L-Trp are described. Featuring an oxidative double cyclization reaction, and tandem C14 epimerization- lactamization reactions as key steps, the method provides a rapid access to (-)-chaetominine (6a) and analogues. The total syntheses of (-)-chaetominine (6a) are so far the most concise and efficient. Through comprehensive investigation, the stereochemical requirements for the double cyclization reaction were revealed, and the confusion regarding physicochemical properties of this natural product was clarified. Moreover, short pathways to complexity generation, a scenarios revealed for the biosynthesis of fungal peptidyl alkaloid multi-cyclic scaffolds, have been validated through the chemical synthesis. On the basis of these findings, a plausible biosynthetic pathway for (-)-chaetominine (6a) was suggested. Copyright
The four-step total synthesis of (-)-chaetominine
Peng, Qi-Long,Luo, Shi-Peng,Xia, Xiao-Er,Liu, Liang-Xian,Huang, Pei-Qiang
supporting information, p. 1986 - 1988 (2014/03/21)
The total synthesis of the alkaloid (-)-chaetominine (1) has been achieved in four steps with an overall yield of 33.4%. Key features of our strategy include a one-pot cascade indole epoxidation-epoxide ring-opening cyclization-lactamization reaction sequence, and the use of a nitro group as a latent amino group for the one-pot construction of the quinazolinone ring. This constitutes a step economical, redox economical and protecting group-free total synthesis.
