Presentation Title

Total Synthesis of DAB-1

Start Date

November 2016

End Date

November 2016

Location

HUB 302-#146

Type of Presentation

Poster

Abstract

DAB-1 is an example of a class of small organic compounds called iminosugars. These resemble carbohydrates, but instead the ring oxygen is substituted by nitrogen. Its similarity to carbohydrates allows for its easy biological uptake and its specificity has paved the way for the development of several experimental drugs for the treatment of diabetes, cancer, and genetic disorders. Enantiopure compounds are of utmost importance when creating biological drugs; one enantiomer might have the desired biological effects while another enantiomer might have adverse ones. Key steps in the synthesis include an enzymatic cyanohydrin formation that sets the stereochemistry, a ruthenium-based cross metathesis, followed by a palladium catalyzed transposition. Current efforts are dedicated to the formation of lactam.

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Nov 12th, 4:00 PM Nov 12th, 5:00 PM

Total Synthesis of DAB-1

HUB 302-#146

DAB-1 is an example of a class of small organic compounds called iminosugars. These resemble carbohydrates, but instead the ring oxygen is substituted by nitrogen. Its similarity to carbohydrates allows for its easy biological uptake and its specificity has paved the way for the development of several experimental drugs for the treatment of diabetes, cancer, and genetic disorders. Enantiopure compounds are of utmost importance when creating biological drugs; one enantiomer might have the desired biological effects while another enantiomer might have adverse ones. Key steps in the synthesis include an enzymatic cyanohydrin formation that sets the stereochemistry, a ruthenium-based cross metathesis, followed by a palladium catalyzed transposition. Current efforts are dedicated to the formation of lactam.