Synthetic study of biphenylquinolizidine alkaloids I. Asymmetric total synthesis of lasubine I featuring organocatalyzed asymmetric intramolecular aza-Michael addition

[Display omitted] •An organocatalyzed asymmetric intramolecular aza-Michael addition of linear dienone was developed.•A new synthetic method of chiral 4-arylquinolizidinone was developed.•A novel and efficient total synthesis of lythraceous alkaloid, lasubine I, was accomplished. A new procedure for...

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Bibliographic Details
Published in:Tetrahedron letters 2017, Vol.58 (3), p.223-226
Main Authors: Hirama, Taku, Umemura, Takayuki, Kogure, Noriyuki, Kitajima, Mariko, Takayama, Hiromitsu
Format: Article
Language:English
Subjects:
Asymmetric synthesis
aza-Michael addition
Lasubine I
Organocatalyst
Quinolizidine alkaloid
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Summary:[Display omitted] •An organocatalyzed asymmetric intramolecular aza-Michael addition of linear dienone was developed.•A new synthetic method of chiral 4-arylquinolizidinone was developed.•A novel and efficient total synthesis of lythraceous alkaloid, lasubine I, was accomplished. A new procedure for the asymmetric total synthesis of lythraceous alkaloids with a 4-arylquinolizidine skeleton was developed, which involved an organocatalyzed asymmetric intramolecular aza-Michael addition.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2016.12.008