title: Enantioselective Synthesis of (+)-Peganumine A.
abstract: A gram-scale enantioselective total synthesis of (+)-peganumine A was accomplished in 7 steps from commercially available 6-methoxytryptamine. Key steps included (a) a Liebeskind-Srogl cross-coupling; (b) a one-pot construction of the tetracyclic skeleton from an ω-isocyano-γ-oxo-aldehyde via a sequence of an unprecedented C-C bond forming lactamization and a transannular condensation; (c) a one-pot organocatalytic process merging two achiral building blocks into an octacyclic structure via a sequence of enantioselective Pictet-Spengler reaction followed by a transannular cyclization. This last reaction created two spirocycles and a 2,7-diazabicyclo[2.2.1]heptan-3-one unit with excellent control of both the absolute and relative stereochemistry of the two newly created quaternary stereocenters.
authors: Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne , EPFL-SB-ISIC-LSPN, BCH5304, CH-1015 Lausanne, Switzerland.
authors: Cyril
authors: C
authors: Piemontesi
authors: Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne , EPFL-SB-ISIC-LSPN, BCH5304, CH-1015 Lausanne, Switzerland.
authors: Qian
authors: Q
authors: Wang
authors: Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne , EPFL-SB-ISIC-LSPN, BCH5304, CH-1015 Lausanne, Switzerland.
authors: Jieping
authors: J
authors: Zhu
mesh_terms: D002243:Carbolines / Q000138:chemical synthesis* / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D013237:Stereoisomerism
chemical_list: D002243:Carbolines; D002264:Carboxylic Acids; C000592085:peganumine A