Biomimetic Enantioselective Total Synthesis of (−)-Siccanin via the Pd-Catalyzed Asymmetric Allylic Alkylation (AAA) and Sequential Radical Cyclizations

2004 ◽  
Vol 126 (39) ◽  
pp. 12565-12579 ◽  
Author(s):  
Barry M. Trost ◽  
Hong C. Shen ◽  
Jean-Philippe Surivet
Keyword(s):  
Total Synthesis ◽  
Allylic Alkylation ◽  
Radical Cyclizations ◽  
Asymmetric Allylic Alkylation ◽  
Enantioselective Total Synthesis

Total Synthesis of (–)-Strempeliopine via Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation

2021 ◽  
Author(s):  
Yi An ◽  
Mengjuan Wu ◽  
Weijian Li ◽  
Yaling Li ◽  
Zhenzhen Wang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Allylic Alkylation ◽  
Asymmetric Allylic Alkylation ◽  
Enantioselective Total Synthesis ◽  
Synthetic Strategy ◽  
Palladium Catalyzed ◽  
The Absolute ◽  
Set Up

Reported herein a concise and enantioselective total synthesis of Schizozygine alkaloids (–)-strempeliopine. This synthetic strategy features a palladium-catalyzed decarboxylative asymmetric allylic alkylation of N-benzoyl lactam to set up the absolute...

scholarly journals Enantioselective Total Synthesis of (–)-Myrifabral A and B

2020 ◽  
Author(s):  
Tyler J. Fulton ◽  
Anthony Chen ◽  
Michael Bartberger ◽  
Brian Stoltz
Keyword(s):  
Total Synthesis ◽  
Allylic Alkylation ◽  
Enantioselective Total Synthesis ◽  
Cross Metathesis ◽  
Quaternary Center ◽  
Tricyclic Core ◽  
Iminium Ion ◽  
Palladium Catalyzed

<p>A catalytic enantioselective approach to the myrioneuron alkaloids (–)-myrifabral A and (–)-myrifabral B is described. The synthesis was enabled by a palladium-catalyzed enantioselective allylic alkylation, that generates the C(10) all-carbon quaternary center. A key N-acyl iminium ion cyclization forged the cyclohexane fused tricyclic core, while vinyl boronate cross metathesis and oxidation afforded the lactol ring of (–)-myrifabral A. Adaptation of previously reported conditions allowed for the conversion of (–)-myrifabral A to (–)-myrifabral B.</p>

scholarly journals A catalytic asymmetric total synthesis of (−)-perophoramidine

2015 ◽  
Vol 6 (1) ◽  
pp. 349-353 ◽  
Author(s):  
B. M. Trost ◽  
M. Osipov ◽  
S. Krüger ◽  
Y. Zhang
Keyword(s):  
Total Synthesis ◽  
Allylic Alkylation ◽  
Asymmetric Total Synthesis ◽  
Asymmetric Allylic Alkylation ◽  
Catalytic Asymmetric ◽  
Key Steps

We describe a catalytic asymmetric total synthesis of the ascidian alkaloid (−)-perophoramidine employing a Mo-catalyzed asymmetric allylic alkylation and unprecedented imino ether allylation as key steps.

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