title: Concise, stereocontrolled synthesis of the citrinadin B core architecture.
abstract: A concise, stereocontrolled synthesis of the citrinadin B core architecture from scalemic, readily available starting materials is disclosed. Highlights include ready access to both cyclic tryptophan tautomer and trans-2,6-disubstituted piperidine fragments, an efficient, stereoretentive mixed Claisen acylation for the coupling of these halves, and further diastereoselective carbonyl addition and oxidative rearrangement for assembly of the core.
authors: Frick Laboratory, Department of Chemistry, Princeton University, Princeton, New Jersey 08544, USA.
authors: Carlos A
authors: CA
authors: Guerrero
authors: Erik J
authors: EJ
authors: Sorensen
mesh_terms: D004952:Esters / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D004952:Esters; D026121:Indole Alkaloids; C503673:citrinadin A