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 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>

Novel Chiral Ligands for Palladium-catalyzed Asymmetric Allylic Alkylation/ Asymmetric Tsuji-Trost Reaction: A Review

2019 ◽  
Vol 23 (11) ◽  
pp. 1168-1213 ◽  
Author(s):  
Samar Noreen ◽  
Ameer Fawad Zahoor ◽  
Sajjad Ahmad ◽  
Irum Shahzadi ◽  
Ali Irfan ◽  
...  
Keyword(s):  
Asymmetric Catalysis ◽  
Enantioselective Synthesis ◽  
Chiral Ligands ◽  
Allylic Alkylation ◽  
Research Groups ◽  
Asymmetric Allylic Alkylation ◽  
Catalytic Potential ◽  
Long Time ◽  
Palladium Catalyzed ◽  
Alkylation Reactions

Background: Asymmetric catalysis holds a prestigious role in organic syntheses since a long time and chiral inductors such as ligands have been used to achieve the utmost desired results at this pitch. The asymmetric version of Tsuji-Trost allylation has played a crucial role in enantioselective synthesis. Various chiral ligands have been known for Pdcatalyzed Asymmetric Allylic Alkylation (AAA) reactions and exhibited excellent catalytic potential. The use of chiral ligands as asymmetric inductors has widened the scope of Tsuji-Trost allylic alkylation reactions. Conclusion: Therefore, in this review article, a variety of chiral inductors or ligands have been focused for palladium catalyzed asymmetric allylic alkylation (Tsuji-Trost allylation) and in this regard, recently reported literature (2013-2017) has been described. The use of ligands causes the induction of enantiodiscrimination to the allylated products, therefore, the syntheses of various kinds of ligands have been targeted by many research groups to employ in Pd-catalyzed AAA reactions.

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