6533b828fe1ef96bd12883eb
RESEARCH PRODUCT
Double asymmetric intramolecular aza-Michael reaction: a convenient strategy for the synthesis of quinolizidine alkaloids.
Javier TorresMarcos EscolanoCarlos Del PozoGloria Alzuet PiñaMaría Sánchez-rosellósubject
Turn (biochemistry)chemistry.chemical_compoundQuinolizidineStereochemistryChemistryIntramolecular forceOrganic ChemistrySalt metathesis reactionMichael reactionTotal synthesisMoietyPhysical and Theoretical ChemistryBiochemistrydescription
A new methodology to access the quinolizidine skeleton in an asymmetric fashion was devised. It involves two consecutive intramolecular aza-Michael reactions of sulfinyl amines bearing a bis-enone moiety, in turn generated by a monodirectional cross metathesis reaction. The sequence, which takes place with excellent yields and diastereocontrol, was applied to the total synthesis of alkaloids lasubine I and myrtine.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2021-09-29 | Organicbiomolecular chemistry |