Model studies on the synthesis of medium-sized and large carbocycles using the Ireland enolate Claisen rearrangement

Author(s):  
Andrew G. Cameron ◽  
David W. Knight
1983 ◽  
Vol 36 (4) ◽  
pp. 803 ◽  
Author(s):  
IK Boddy ◽  
RC Cambie ◽  
G Dixon ◽  
PS Rutledge ◽  
PD Woodgate

The Claisen rearrangement of some allyl naphthalen-1-yl ethers has been examined, together with methods for modification of the resulting 2-ally1 side chain. Isomerization of the C-allyl substituent to a prop-1-enyl group followed by ozonolysis gives a formyl derivative, while ozonolysis of a 2-(2-methylprop-2-enyl) moiety or mercuriation of a 2-(2-chloroprop-2-enyl) substituent leads to an acetonyl derivative. Treatment of phenols with iodine(I) acetate and an excess of silver(I) acetate gives 4-hydroxyaryl acetates, probably via dienone intermediates.


2010 ◽  
Vol 51 (34) ◽  
pp. 4543-4546 ◽  
Author(s):  
Kenshu Fujiwara ◽  
Keita Tanaka ◽  
Yasushi Katagiri ◽  
Hidetoshi Kawai ◽  
Takanori Suzuki

2014 ◽  
Vol 10 ◽  
pp. 194-208 ◽  
Author(s):  
Hanna Bruss ◽  
Hannah Schuster ◽  
Rémi Martinez ◽  
Markus Kaiser ◽  
Andrey P Antonchick ◽  
...  

Synthetic investigations towards the structurally complex and highly decorated framework of B-seco limonoid natural products by means of a [3,3]-sigmatropic rearrangement are described. Detailed model studies reveal, that an Ireland–Claisen rearrangement can be employed to construct the central C9–C10 bond thereby giving access to the B-seco limonoid scaffold. However, application of the developed strategy ended up failing in more complex and sterically demanding systems.


1995 ◽  
Vol 74 (03) ◽  
pp. 868-873 ◽  
Author(s):  
Silvana Arrighi ◽  
Roberta Rossi ◽  
Maria Giuseppina Borri ◽  
Vladimir Lesnikov ◽  
Marina Lesnikov ◽  
...  

SummaryTo improve the safety of plasma derived factor VIII (FVIII) concentrate, we introduced a final super heat treatment (100° C for 30 min) as additional virus inactivation step applied to a lyophilized, highly purified FVIII concentrate (100 IU/mg of proteins) already virus inactivated using the solvent/detergent (SID) method during the manufacturing process.The efficiency of the super heat treatment was demonstrated in inactivating two non-lipid enveloped viruses (Hepatitis A virus and Poliovirus 1). The loss of FVIII procoagulant activity during the super heat treatment was of about 15%, estimated both by clotting and chromogenic assays. No substantial changes were observed in physical, biochemical and immunological characteristics of the heat treated FVIII concentrate in comparison with those of the FVIII before heat treatment.


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