ChemInform Abstract: SYNTHESIS APPLICATIONS OF AZA-COPE REARRANGEMENTS. PART 14. TOTAL SYNTHESIS OF (-)-CRININE. USE OF TANDEM CATIONIC AZA-COPE REARRANGEMENT/MANNICH CYCLIZATIONS FOR THE SYNTHESIS OF ENANTIOMERICALLY PURE AMARYLLIDACEAE ALKALOIDS

1985 ◽  
Vol 16 (35) ◽  
Author(s):  
L. E. OVERMAN ◽  
S. SUGAI
Keyword(s):  
Total Synthesis ◽  
Cope Rearrangement ◽  
Enantiomerically Pure ◽  
Amaryllidaceae Alkaloids ◽  
Cope Rearrangements

Aromatic Cope Rearrangements

2021 ◽  
Author(s):  
Breanna Tomiczek ◽  
Alexander Grenning
Keyword(s):  
Cope Rearrangement ◽  
Aromatic System ◽  
Cope Rearrangements

Reviewed herein is the aromatic Cope rearrangement, a Cope rearrangement where one (or both) of the alkenes of the 1,5-diene are part of a greater aromatic system. While the Cope...

scholarly journals Diastereoselective Total Synthesis of (+)-Raputindole A: An Iridium- Catalyzed Cyclization Approach

2020 ◽  
Author(s):  
Ronaldo Pilli ◽  
Juliana Lira Luna Freire Regueira ◽  
Luiz Fernando Silva Jr.
Keyword(s):  
Total Synthesis ◽  
Heck Reaction ◽  
Enzymatic Resolution ◽  
Enantiomerically Pure ◽  
Tricyclic Core ◽  
Benzylic Alcohol ◽  
Convergent Approach

This work describes the total synthesis of Raputindole A <b>(1)</b> through a convergent approach which features: 1) an iridium-catalyzed cyclization to assembly the tricyclic core of the northern part, 2) enzymatic resolution to secure the preparation of enantiomerically pure benzylic alcohol, 3) installation of the butenyl substituent via methallylation of the corresponding benzylic carbocation and coupling of the northern and southern parts via Heck reaction. (+)-Raputindole A <b>(1)</b> was prepared in 10 steps (LLS) and 10% overall yield.

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