A biomimetic route for construction of the [4+2] and [3+2] core skeletons of dimeric pyrrole-imidazole alkaloids and asymmetric synthesis of ageliferins.
The pyrrole-imidazole alkaloids have fascinated chemists for decades because of their unique structures. The high nitrogen and halogen contents and the densely functionalized skeletons make their laboratory synthesis challenging. We describe herein an oxidative method for accessing the core skeletons of two classes of pyrrole-imidazole dimers. This synthetic strategy was inspired by the putative biosynthesis pathways and its development was facilitated by computational studies. Using this method, we have successfully prepared ageliferin, bromoageliferin, and dibromoageliferin in their natural enantiomeric form.
Division of Chemistry, Department of Biochemistry, The University of Texas Southwestern Medical Center, Dallas, 75390-9038, United States.
Xiao
X
Wang
Xiaolei
X
Wang
Xianghui
X
Tan
Jianming
J
Lu
Kevin W
KW
Cormier
Zhiqiang
Z
Ma
Chuo
C
Chen
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D040761:Biomimetic Materials / Q000737:chemistry*; D003500:Cyclization; D019281:Dimerization; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D011789:Quantum Theory
D000470:Alkaloids; D007093:Imidazoles; D011758:Pyrroles; C514118:ageliferin