A convergent approach to cyclopeptide alkaloids: total synthesis of sanjoinine G1.
A general strategy for the synthesis of cyclopeptide alkaloids containing an endocyclic aryl-alkyl ether bond has been developed featuring a key intramolecular S(N)Ar reaction. The importance of the N-terminal protective group in the realization of such a strategy is documented. From the appropriate amino acid constituents, the natural sanjoinine G1, a 14-membered para cyclophane, has been synthesized in seven steps with 21% overall yield.
Temal-Laïb
Taoues
T
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette, France.
Chastanet
Jacqueline
J
Zhu
Jieping
J
D000470:Alkaloids / Q000737:chemistry*; D008956:Models, Chemical; D010456:Peptides, Cyclic / Q000138:chemical synthesis*
D000470:Alkaloids; D010456:Peptides, Cyclic; C450941:sanjoinine G1