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. 2016 Apr 1;18(7):1558-61.
doi: 10.1021/acs.orglett.6b00374. Epub 2016 Mar 21.

Efficient Strategy for the Construction of Both Enantiomers of the Octahydropyrroloquinolinone Ring System: Total Synthesis of (+)-Aspidospermidine

Ganesh Pandey  1 , Shiva Kumar Burugu  1   2 , Pushpendra Singh  1
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Efficient Strategy for the Construction of Both Enantiomers of the Octahydropyrroloquinolinone Ring System: Total Synthesis of (+)-Aspidospermidine

Ganesh Pandey et al. Org Lett. .

Abstract

An efficient and highly stereoselective intramolecular [3 + 2] cycloaddition of nonstabilized azomethine ylide generated from a designed bicyclic aminal precursor is reported for the synthesis of both (-)- and (+)-octahydropyrroloquinolinone. One of the enantiomers is further advanced to accomplish the total synthesis of (+)-aspidospermidine.

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