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A concise, linear synthesis of the Stemona alkaloid (+/-)-neostenine is reported. Key features include an organocopper-mediated bislactone C2-desymmetrization for the stereoselective construction of the cyclohexane-lactone C,D-rings. The assembly of the fused pyrrolo[1,2-a]azepine core was achieved by application of a [5 + 2] maleimide photocycloaddition. A custom FEP flow reactor was used to successfully overcome the scale limitations imposed by a classical immersion well batch reactor. The synthesis was completed in 14 steps from furan, in 9.5% overall yield, without the use of any protecting groups.

Original publication

DOI

10.1021/jo801108h

Type

Journal article

Journal

J Org Chem

Publication Date

05/09/2008

Volume

73

Pages

6497 - 6505

Keywords

Alkaloids, Azepines, Cyclohexanes, Furans, Lactones, Maleimides, Models, Chemical, Photochemistry, Pyrroles, Stemonaceae, Stereoisomerism