Stereocontrolled Annulations of Indolo[2,3-a]quinolizidine-Derived Lactams with a Silylated Nazarov Reagent: Access to Allo and Epiallo Yohimbine-Type Derivatives.

@article{Arioli2015StereocontrolledAO,
  title={Stereocontrolled Annulations of Indolo[2,3-a]quinolizidine-Derived Lactams with a Silylated Nazarov Reagent: Access to Allo and Epiallo Yohimbine-Type Derivatives.},
  author={Federica Arioli and Maria P{\'e}rez and Celeste Are and Carolina Estarellas and Francisco Javier Luque and Joan Bosch and Mercedes Amat},
  journal={Chemistry},
  year={2015},
  volume={21 38},
  pages={
          13382-9
        }
}
The facial selectivity of double Michael addition reactions of the silylated Nazarov reagent 4 to unsaturated indolo[2,3-a]quinolizidine lactams 3 has been studied. Pentacyclic 3-H/15-H trans adducts 5 are generated from Nind -unsubstituted lactams, but the corresponding cis isomers 6 are formed when the indole nitrogen has a tert-butyloxycarbonyl (Boc) substituent. This reversal in the facial selectivity of the annulation has been rationalized by means of theoretical calculations, which… 
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Origin of the Base‐Dependent Facial Selectivity in Annulation Reactions of Nazarov‐Type Reagents with Unsaturated Indolo[2,3‐a]quinolizidine Lactams
The methyl-substituted Nazarov reagent 4 stereoselectively reacts with Nind-Boc indoloquinolizidine lactams to give the expected H-3/H-15 cis pentacyclic yohimbine-type adducts when using DBU as the…
Stereocontrolled Annulations of Indolo[2,3-a]quinolizidine-Derived Lactams with a Silylated Nazarov Reagent: Access to Allo and Epiallo Yohimbine-Type Derivatives.
The facial selectivity of double Michael addition of the silylated Nazarov reagent (II) and title compounds (I) is studied.
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Base-catalyzed annulation reactions of 5,6-dihydro-2(1H)-pyridones with Nazarov-type reagents with stereoselectively provides functionalized cis-perhydroisoquinolin-1-ones.
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This compound represents a hit compound for the development of novel NMDA receptor antagonists with potential applications in neurodegenerative disorders associated with overactivation of NMDA receptors.
Total Syntheses of Naucleamides A-C and E, Geissoschizine, Geissoschizol, (E)-Isositsirikine, and 16-epi-(E)-Isositsirikine.
A divergent approach for the enantioselective total synthesis of eight monoterpenoid indole alkaloids was developed. The approach allows the first total syntheses of naucleamides A-C and E in only…
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