Enantioselective total synthesis of (−)-kainic acid and (+)-acromelic acid C via Rh(i)-catalyzed asymmetric enyne cycloisomerization

2018 ◽  
Vol 54 (7) ◽  
pp. 727-730 ◽  
Author(s):  
Honghui Lei ◽  
Shan Xin ◽  
Yifan Qiu ◽  
Xumu Zhang
Keyword(s):  
Total Synthesis ◽  
Kainic Acid ◽  
Enantioselective Synthesis ◽  
Enantioselective Total Synthesis ◽  
Synthetic Strategy

A diversity-oriented synthetic strategy for the enantioselective synthesis of (−)-kainic acid and (+)-acromelic acid C is presented.

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 Development of a Divergent Route to Erythrina Alkaloids

Synlett ◽  
2020 ◽  
Vol 31 (04) ◽  
pp. 327-333 ◽  
Author(s):  
Jesper L. Kristensen ◽  
Sebastian Clementson ◽  
Mikkel Jessing ◽  
Paulo J. Vital
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
19Th Century ◽  
First Generation ◽  
Second Generation ◽  
Enantioselective Synthesis ◽  
Third Generation ◽  
Synthetic Strategy ◽  
Erythrina Alkaloids ◽  
The 19Th Century

Erythrina alkaloids were identified at the end of the 19th century and today, more than 100 members of the erythrinane family have been isolated. They are characterized by a unique tetracyclic, α-tertiary spiroamine scaffold. Herein we detail our efforts towards the development of a divergent enantioselective synthesis of (+)-dihydro-β-erythroidine (DHβE) – one of the most prominent members of this intriguing family of natural products.1 Introduction2 Synthetic Strategy2.1 First Generation2.2 Second Generation2.3 Third Generation2.3.1 Radical Endgame2.3.2 Completion of the Total Synthesis3 Conclusion

Enantioselective total synthesis of (+)-arborescidine C and related tetracyclic indole alkaloids using organocatalysis

2017 ◽  
Vol 15 (16) ◽  
pp. 3408-3412 ◽  
Author(s):  
Vishal M. Sheth ◽  
Bor-Cherng Hong ◽  
Gene-Hsiang Lee
Keyword(s):  
Total Synthesis ◽  
Indole Alkaloids ◽  
Enantioselective Synthesis ◽  
Cyclization Reaction ◽  
Enantioselective Total Synthesis

Enantioselective synthesis of (+)-arborescidine C was achieved by the key step of Pictet–Spengler cyclization reaction with a Jacobsen-type thiourea organocatalyst.

Enantioselective Total Synthesis of (−)-α-Kainic Acid

2010 ◽  
Vol 12 (5) ◽  
pp. 1108-1111 ◽  
Author(s):  
Andreas Farwick ◽  
Günter Helmchen
Keyword(s):  
Total Synthesis ◽  
Kainic Acid ◽  
Enantioselective Total Synthesis

scholarly journals Towards stereochemical control: A short formal enantioselective total synthesis of pumiliotoxins 251D and 237A

2013 ◽  
Vol 9 ◽  
pp. 2358-2366 ◽  
Author(s):  
Jie Zhang ◽  
Hong-Kui Zhang ◽  
Pei-Qiang Huang
Keyword(s):  
Total Synthesis ◽  
Enantioselective Synthesis ◽  
Ring Closure ◽  
Enantioselective Total Synthesis ◽  
Stereochemical Control ◽  
Stereoselective Addition ◽  
Methylmagnesium Iodide

A concise enantioselective synthesis of the advanced intermediate 5 for the synthesis of pumiliotoxins (Gallagher’s intermediate) is described. The synthesis started from the regio- and trans-diastereoselective (dr = 98:2) reductive 3-butenylation of (R)-3-(tert-butyldimethylsilyloxy)glutarimide 14. After O-desilylation and Dess–Martin oxidation, the resulting keto-lactam 10 was subjected to a highly trans-stereoselective addition of the methylmagnesium iodide to give carbinol 11 as sole diastereomer. An efficient ring closure procedure consisting of ozonolysis and reductive dehydroxylation provided the indolizidine derivative 5, which completed the formal enantioselective total synthesis of pumiliotoxins 251D and 237A.

scholarly journals Enantioselective total synthesis of (R)-(−)-complanine

2012 ◽  
Vol 8 ◽  
pp. 1695-1699 ◽  
Author(s):  
Krystal A D Kamanos ◽  
Jonathan M Withey
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Causative Agent ◽  
Enantioselective Synthesis ◽  
Marine Natural Product ◽  
Enantioselective Total Synthesis ◽  
Efficient Access

A route is described for the enantioselective synthesis of (R)-(−)-complanine, a marine natural product isolated from Eurythoe complanata, and known to be a causative agent in inflammation. An organocatalytic, asymmetric oxyamination of a homoconjugated all-Z-dienal intermediate provides versatile and efficient access to the natural product.

scholarly journals Enantioselective total synthesis of (−)-colchicine, (+)-demecolcinone and metacolchicine: determination of the absolute configurations of the latter two alkaloids

2017 ◽  
Vol 8 (7) ◽  
pp. 4961-4966 ◽  
Author(s):  
Bo Chen ◽  
Xin Liu ◽  
Ya-Jian Hu ◽  
Dong-Mei Zhang ◽  
Lijuan Deng ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Enantioselective Synthesis ◽  
Enantioselective Total Synthesis ◽  
The Absolute

A highly concise, enantioselective synthesis of (−)-colchicine, the first syntheses of (+)-demecolcinone and metacolchicine, was reported.

Enantioselective total synthesis and biological evaluation of (−)-solanacol

2018 ◽  
Vol 16 (30) ◽  
pp. 5500-5507 ◽  
Author(s):  
L. J. Bromhead ◽  
A. R. Norman ◽  
K. C. Snowden ◽  
B. J. Janssen ◽  
C. S. P. McErlean
Keyword(s):  
Total Synthesis ◽  
Phenyl Ring ◽  
Biological Evaluation ◽  
Enantioselective Synthesis ◽  
Enantioselective Total Synthesis ◽  
Synthesis And Biological Evaluation

An enantioselective synthesis of the phenyl ring-containing strioglactone, (−)-solanocol, is described.

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