1305333-11-2Relevant academic research and scientific papers
Novel entry to the tricyclic core of stemofoline and didehydrostemofoline
Dietz, Jochen,Martin, Stephen F.
, p. 2048 - 2050 (2011/05/09)
A novel approach to the tricyclic core of the Stemona alkaloids stemofoline and didehydrostemofoline has been discovered that features an intramolecular (3+2) dipolar cycloaddition of an unactivated carbon-carbon double bond with an azomethine ylide; the azomethine ylide was generated by an unprecedented reaction that occurred during a Swern oxidation of an α-(N-cyanomethyl)- β-hydroxy ester. In separate experiments, the efficacy of introducing the requisite oxygen functionality at C(8) and the 1-butenyl side chain at C(3) was established.
