Enantioselective Total Synthesis of atrans-Hydrindane Rings/Side-Chain Building-Block of Vitamin D− Asymmetric Induction in an Acid-Catalyzed Conjugate-Addition Reaction

2004 ◽  
Vol 2004 (4) ◽  
pp. 783-799 ◽  
Author(s):  
Evgueni Gorobets ◽  
Viatcheslav Stepanenko ◽  
Jerzy Wicha
Keyword(s):  
Vitamin D ◽  
Total Synthesis ◽  
Building Block ◽  
Addition Reaction ◽  
Conjugate Addition ◽  
Asymmetric Induction ◽  
Side Chain ◽  
Enantioselective Total Synthesis ◽  
Acid Catalyzed

A Concise Total Synthesis of (±)-Mesembrine

Synlett ◽  
2018 ◽  
Vol 29 (09) ◽  
pp. 1203-1206 ◽  
Author(s):  
Hyoungsu Kim ◽  
Hosam Choi ◽  
Kiyoun Lee
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Addition Reaction ◽  
Conjugate Addition ◽  
Allylic Oxidation ◽  
Quaternary Stereocenter

A concise total synthesis of (±)-mesembrine has been successfully accomplished in seven steps and 24% overall yield from commercially available 3-ethoxy-2-cyclohexen-1-one. Central to the assembly of the skeleton of mesembrine are a Johnson–Claisen rearrangement for the formation of the benzylic quaternary stereocenter and direct allylic oxidation to generate the substrate for the amidation/transannular aza-conjugate addition reaction.

Asymmetric organocatalytic synthesis of chiral 3,3-disubstituted oxindolesviaa 1,6-conjugate addition reaction

2018 ◽  
Vol 16 (29) ◽  
pp. 5301-5309 ◽  
Author(s):  
Abdul Rahman ◽  
Qiaoxia Zhou ◽  
Xufeng Lin
Keyword(s):  
Phosphoric Acid ◽  
Addition Reaction ◽  
Conjugate Addition ◽  
Quinone Methides ◽  
Acid Catalyzed

The chiral spirocyclic phosphoric acid-catalyzed enantioselective 1,6-conjugate addition reaction ofpara-quinone methides derived fromN-unprotected isatins with indoles was developed.

Total Synthesis of (–)-Aristoquinoline via an Intramolecular Nitrilium Ion Cyclization

Synthesis ◽  
2021 ◽  
Author(s):  
Keith P. Reber ◽  
Priyansh D. Gujarati
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Building Block ◽  
Spectroscopic Properties ◽  
Ring System ◽  
Synthetic Route ◽  
Enantioselective Total Synthesis ◽  
Key Steps

AbstractThe enantioselective total synthesis of the alkaloid aristoquinoline has been achieved in seven steps and 26% overall yield. A new preparation of the useful synthetic building block (–)-α-terpinyl amine was also developed in order to avoid stoichiometric mercury reagents or azide-containing intermediates. Key steps in the optimized synthetic route include an intramolecular nitrilium ion cyclization to form the characteristic azabicyclo[3.3.1]nonane ring system and a dia­stereoselective reduction of the resulting imine mixture to afford the natural product. An isomer of aristoquinoline containing an exocyclic alkene was also obtained and found to exhibit unusual chromatographic and spectroscopic properties.

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