Double asymmetric intramolecular aza-Michael reaction: a convenient strategy for the synthesis of quinolizidine alkaloids

被引：0

作者：

Torres, Javier ^{[1
]}

Escolano, Marcos ^{[1
]}

Alzuet-Pina, Gloria ^{[2
]}

Sanchez-Rosello, Maria ^{[1
]}

del Pozo, Carlos ^{[1
]}

机构：

[1] Univ Valencia, Dept Organ Chem, Vicente Andres Estelles S-N, Burjassot 46100, Spain

[2] Univ Valencia, Dept Inorgan Chem, Vicente Andres Estelles S-N, Burjassot 46100, Spain

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2021年 / 19卷 / 40期

关键词：

FUNCTIONALIZED TRANS-2,6-DISUBSTITUTED PIPERIDINES; FORMAL TOTAL-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; STEREODIVERGENT SYNTHESIS; LYCOPODIUM ALKALOIDS; (-)-LASUBINE II; SENEPODINE-G; INDOLIZIDINE; (+)-MYRTINE; CONSTRUCTION;

D O I：

10.1039/d1ob01488a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：8740 / 8745

页数：6

共 63 条

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