Stereoselective addition of methylcuprates to a 2-formyl-cyclohexa-2,5-dienone system. A stereoselective total synthesis of racemic β-vetivone

1974 ◽  
pp. 1005-1006 ◽  
Author(s):  
Giuliano Bozzato ◽  
Jean-Pierre Bachmann ◽  
Mario Pesaro
Keyword(s):  
Total Synthesis ◽  
System A ◽  
Stereoselective Addition

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.

ChemInform Abstract: An Asymmetric Route to the Conanine BCDE Ring System. A Formal Total Synthesis of (+)-Conessine.

ChemInform ◽  
2010 ◽  
Vol 28 (8) ◽  
pp. no-no
Author(s):  
M. E. KOPACH ◽  
A. H. FRAY ◽  
A. I. MEYERS
Keyword(s):  
Total Synthesis ◽  
Ring System ◽  
System A
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