title: Concise synthesis of the Erythrina alkaloid 3-demethoxyerythratidinone via combined rhodium catalysis.
abstract: The total synthesis of the erythrina alkaloid 3-demethoxyerythratidinone has been achieved via a strategy based on combined rhodium catalysis. The catalytic tandem cyclization effected by the interplay of alkynyl and vinylidene rhodium species allows for efficient access to the A and B rings of the tetracyclic erythrinane skeleton in a single step. The synthesis also features rapid preparation of the requisite precursor for the double ring closure and thus has been completed in only 7 total steps in 41% overall yield.
authors.affiliation: Department of Chemistry, Princeton University, Princeton, New Jersey 08544, USA.
authors.forename: Jung Min
authors.initials: JM
authors.lastname: Joo
authors.forename: Ramoncito A
authors.initials: RA
authors.lastname: David
authors.forename: Yu
authors.initials: Y
authors.lastname: Yuan
authors.forename: Chulbom
authors.initials: C
authors.lastname: Lee
mesh_terms: D002384:Catalysis; D003500:Cyclization; D004895:Erythrina / Q000737:chemistry*; D026121:Indole Alkaloids / Q000138:chemical synthesis*; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*
chemical_list: C514302:3-demethoxyerythratidinone; D026121:Indole Alkaloids; D012238:Rhodium