A convenient one-pot procedure to afford bicyclic molecules by stereospecific iron carbonyl mediated [6 + 2] ene-type cyclization: a possible approach to gelsemine.
A convenient one-pot procedure to prepare angularly substituted bicyclic and tricyclic molecules with excellent diastereoselectivity in good yield was developed, by Fe(CO)5 promoted cyclization. Three transformations (complexation, isomerization, and cyclization) were realized in a single operation. The product of this reaction may be a precursor for synthesis of the alkaloid gelsemine.
Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA. ajp4@cwru.edu
Anthony J
AJ
Pearson
Xiaolong
X
Wang
D000470:Alkaloids / Q000138:chemical synthesis*; D000475:Alkenes / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D003500:Cyclization; D013237:Stereoisomerism
D000470:Alkaloids; D000475:Alkenes; D001643:Bridged Bicyclo Compounds; C063230:gelsemine