title: A synthesis of pseudoconhydrine and its epimer via hydroformylation and dihydroxylation.
abstract: A synthesis of the alkaloid pseudoconhydrine and its epimer has been achieved using tandem hydroformylation-condensation to form the six-membered ring and stereoselective dihydroxylation to introduce oxygenation. The stereoselectivity of dihydroxylation can be explained by lipophilic and electrostatic effects, supported by DFT calculations. The alkaloids can be obtained either by regioselective dehydroxylation or by rearrangement, followed by reduction.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371. roderick@ntu.edu.sg
authors.forename: Roderick W
authors.initials: RW
authors.lastname: Bates
authors.forename: K
authors.initials: K
authors.lastname: Sivarajan
authors.forename: Bernd F
authors.initials: BF
authors.lastname: Straub
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D010880:Piperidines; C568413:pseudoconhydrine