Asymmetric Total Synthesis of (−)-Scabronine G via Intramolecular Double Michael Reaction and Prins Cyclization

2011 ◽  
Vol 13 (11) ◽  
pp. 2864-2867 ◽  
Author(s):  
Naoki Kanoh ◽  
Kohei Sakanishi ◽  
Emiko Iimori ◽  
Ken’ichi Nishimura ◽  
Yoshiharu Iwabuchi
Keyword(s):  
Total Synthesis ◽  
Michael Reaction ◽  
Asymmetric Total Synthesis ◽  
Prins Cyclization

Catalytic Asymmetric Total Synthesis of Chimonanthine, Folicanthine, and Calycanthine through Double Michael Reaction of Bisoxindole

2012 ◽  
Vol 124 (21) ◽  
pp. 5307-5311 ◽  
Author(s):  
Harunobu Mitsunuma ◽  
Masakatsu Shibasaki ◽  
Motomu Kanai ◽  
Shigeki Matsunaga
Keyword(s):  
Total Synthesis ◽  
Michael Reaction ◽  
Asymmetric Total Synthesis ◽  
Catalytic Asymmetric

scholarly journals Asymmetric Total Synthesis of Arcutinidine and Arcutinine

2019 ◽  
Author(s):  
Shupeng Zhou ◽  
Kaifu Xia ◽  
Ang Li
Keyword(s):  
Total Synthesis ◽  
Final Stage ◽  
Reductive Amination ◽  
Diels Alder ◽  
Diterpenoid Alkaloids ◽  
Asymmetric Total Synthesis ◽  
Prins Cyclization ◽  
The Core

We have accomplished the asymmetric total synthesis of arcutinidine and arcutinine, two arcutine-type C20-diterpenoid alkaloids. A pentacyclic intermediate was rapidly assembled by using two Diels−Alder reactions. A cascade sequence of Prins cyclization and Wagner−Meerwein rearrangement was then developed to construct the core of arcutinidine, which was further elaborated into an oxygenated pentacycle through a scalable route. Chemoselective reductive amination followed by spontaneous imine formation furnished the pyrroline motif at a final stage.

Asymmetric Total Synthesis of Arcutinidine and Arcutinine

2019 ◽  
Author(s):  
Shupeng Zhou ◽  
Kaifu Xia ◽  
Ang Li
Keyword(s):  
Total Synthesis ◽  
Final Stage ◽  
Reductive Amination ◽  
Diels Alder ◽  
Diterpenoid Alkaloids ◽  
Asymmetric Total Synthesis ◽  
Prins Cyclization ◽  
The Core

We have accomplished the asymmetric total synthesis of arcutinidine and arcutinine, two arcutine-type C20-diterpenoid alkaloids. A pentacyclic intermediate was rapidly assembled by using two Diels−Alder reactions. A cascade sequence of Prins cyclization and Wagner−Meerwein rearrangement was then developed to construct the core of arcutinidine, which was further elaborated into an oxygenated pentacycle through a scalable route. Chemoselective reductive amination followed by spontaneous imine formation furnished the pyrroline motif at a final stage.

Asymmetric total synthesis of atisine via intramolecular double Michael reaction

1990 ◽  
Vol 112 (3) ◽  
pp. 1164-1171 ◽  
Author(s):  
Masataka Ihara ◽  
Makoto Suzuki ◽  
Keiichiro Fukumoto ◽  
Chizuko Kabuto
Keyword(s):  
Total Synthesis ◽  
Michael Reaction ◽  
Asymmetric Total Synthesis
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