Efficient and stereoselective dimerization of pyrroloindolizine derivatives inspired by a hypothesis for the biosynthesis of complex myrmicarin alkaloids.
Pyrroloindolizine derivatives participate in efficient and stereoselective homo- and heterodimerization reactions upon treatment with Brønsted or Lewis acids. The distinctive ability of pyrroloindolizines to act as azafulvenium ion precursors provides direct access to both heptacyclic and hexacyclic dimeric products. The inherent reactivity of these structures suggests a concise synthesis of complex myrmicarin alkaloids, via dimerization of pyrroloindolizines, and may have implications for the biosynthesis of these intriguing alkaloids.
Movassaghi
Mohammad
M
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA. movassag@mit.edu
Ondrus
Alison E
AE
Chen
Bin
B
D019281:Dimerization; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D006575:Heterocyclic Compounds, 3-Ring; D011758:Pyrroles; C512230:myrmicarin; C042028:pyrroloindolizine