Stereoselective Cascade Cyclizations with Samarium Diiodide to Tetracyclic Indolines: Precursors of Fluorostrychnines and Brucine

2019 ◽  
Author(s):  
Christine Beemelmanns ◽  
Dominik Nitsch ◽  
Christoph Bentz ◽  
Hans‐Ulrich Reissig
Keyword(s):  
Samarium Diiodide ◽  
Cascade Cyclizations

Samarium Diiodide Catalyzed Radical Cascade Cyclizations that Construct Quaternary Stereocenters

Synlett ◽  
2019 ◽  
Vol 31 (01) ◽  
pp. 45-50 ◽  
Author(s):  
Huan-Ming Huang ◽  
Qiong He ◽  
David J. Procter
Keyword(s):  
Ambient Temperature ◽  
High Selectivity ◽  
Samarium Diiodide ◽  
Mechanistic Studies ◽  
Cascade Cyclizations ◽  
Radical Cascade ◽  
Quaternary Stereocenters ◽  
Quaternary Stereocenter

SmI2-catalyzed radical cascade cyclizations were used to generate complex carbocyclic products bearing quaternary stereocenters with high selectivity. Bicyclic scaffolds containing four contiguous stereocenters and one quaternary stereocenter were obtained in excellent yields (up to 99%) and with high diastereocontrol by using 5 mol% of SmI2 at ambient temperature in the absence of co-reductants or additives. Mechanistic studies support a radical relay mechanism.

Palladium-catalyzed cascade cyclizations involving C–C and C–X bond formation: strategic applications in natural product synthesis

2021 ◽  
Author(s):  
K. R. Holman ◽  
A. M. Stanko ◽  
S. E. Reisman
Keyword(s):  
Natural Product ◽  
Bond Formation ◽  
Natural Product Synthesis ◽  
Cascade Cyclizations ◽  
Palladium Catalyzed ◽  
Multiple Rings

This tutorial review highlights the use of palladium-catalyzed cascade cyclizations in natural product synthesis, focusing on cascades that construct multiple rings and form both C–C and C–X (X = O, N) bonds in a single synthetic operation.

Samarium diiodide in tetrahydropyran : Preparation and some reactions in organic chemistry

1994 ◽  
Vol 35 (11) ◽  
pp. 1723-1726 ◽  
Author(s):  
Jean-Louis Namy ◽  
Marielle Colomb ◽  
Henri B. Kagan
Keyword(s):  
Organic Chemistry ◽  
Samarium Diiodide

ChemInform Abstract: Cascade Cyclizations of Acyclic and Macrocyclic Alkynones: Studies Toward the Synthesis of Phomactin A.

ChemInform ◽  
2014 ◽  
Vol 45 (9) ◽  
pp. no-no
Author(s):  
Jennifer Ciesielski ◽  
Vincent Gandon ◽  
Alison J. Frontier
Keyword(s):  
Cascade Cyclizations ◽  
Phomactin A
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