From catechol to sugar: A new synthetic application of asymmetric catalysis

ORGN 98

Alina Ariosa Alvarez Jr., alina.ariosa@ucd.ie, Padraic McGovern, podgewins@yahoo.com, and Lorna Kennedy, lorna.kennedy@ucd.ie. School of Chemistry and Chemical Biology, University College Dublin, Belfield, -, Dublin, D4, Ireland
The interest in the design and synthesis of natural and unnatural carbohydrates is due to the abundance of carbohydrates in living cells. Several categories of natural products contain deoxysugar moieties that are essential for their biological activities. We now report an efficient short strategy for natural and branched deoxysugar families using catechols as starting material. The key step of the sequence is the in situ substrate controlled formation of lactones in two steps from natural and inexpensive catechols. The advantage of this type of approach is the ability to design a wide range of branched molecules by choosing the appropriate starting material and the protocol of oxidation. We will also feature our current studies into the Sharpless catalytic asymmetric dihydroxylation reaction using Z,Z diene dionate. Details of the reaction behaviour depending on the substituent and its position on the molecule will be discussed.