Formal Synthesis of (+)-Lasubine II and (−)-Subcosine II via Organocatalytic Michael Addition of a Ketone to an α‑Nitrostyrene
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The first examples of an organocatalytic Michael addition of a ketone to in situ generated α-nitrostyrenes are reported. A suitably functionalized γ-nitroketone obtained from the organocatalyzed Michael addition was converted into (+)-2-epi-lasubine II, the immediate synthetic precursor of (+)-lasubine II and (−)-subcosine II (enantiomers of the natural quinolizidine alkaloids). Two of the three stereocenters in (+)-2-epi-lasubine II are set by the Michael reaction.
创建时间:
2016-02-12



