158780-51-9Relevant academic research and scientific papers
Sigmatropic rearrangement of uronic acid derived saccharide allyl ketene acetals. A study of stereochemistry and structural limitations
Werschkun, Barbara,Thiem, Joachim
, p. 121 - 137 (1999)
Allyl ketene acetal Claisen rearrangement of uronic acid derivatives with furanoside structure was studied. Reproducibility of the observed stereodiscrimination was confirmed in the conversion of enantiomeric starting materials. From X-ray structural data
A Synthetic Approach to the Squalestatins and Zaragozic Acids: Introduction of the C5 Stereocentre via an Ester-Enolate Claisen Rearrangement. The X-Ray Crystal Structure of an Intermediate
Gable, Robert W.,McVinish, Leasa M.,Rizzacasa, Mark A.
, p. 1537 - 1544 (2007/10/02)
In an overall plan to synthesize the anti-cholesterol agents the squalestatins and zaragozic acids, introduction of the C5 stereochemistry was achieved via an Ireland-Claisen rearrangement of the allyl ester (7) followed by methylation, which gives the es
Synthetic Studies Towards the Squalestatins and Zaragozic Acids.
McVinish, Leasa M.,Rizzacasa, Mark A.
, p. 923 - 926 (2007/10/02)
A synthesis of a model core system (18) of the squalestatins and zaragozic acids has been achieved from D-mannose.The key steps involve an Ireland-Claisen rearrangement of the allyl ester 5 and a stereoselective epoxidation of the furanoid glycal 12 with
