27261-93-4Relevant articles and documents
Concise, enantioselective total syntheses of both the proposed and revised structures of (?)-versiquinazoline H
Wu, Jiang-Feng,Huang, Pei-Qiang
supporting information, p. 61 - 63 (2019/08/16)
The enantioselective total synthesis of the putative structure of versiquinazoline H and three diastereomers has been achieved, which allowed the revision of the stereochemistry of this natural product. This six-step total synthesis relied on the evolution of the strategy that we previously developed, which features a DMDO-triggered tandem reaction. The modification of the lactamization step resulted in a significant improvement of yield that ensured the efficient total synthesis.
Complexity generation by chemical synthesis: A five-step synthesis of (-)-chaetominine from l-tryptophan and its biosynthetic implications
Xu, Chu-Pei,Luo, Shi-Peng,Wang, Ai-E,Huang, Pei-Qiang
supporting information, p. 2859 - 2863 (2014/05/06)
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). This journal is the Partner Organisations 2014.
