Search

Mailing List

For all the latest news and features, sign up to receive our FREE updates by email:


Practical synthesis of neoponkoranol and its related sulfonium salt, an optimised protocol using isopropylidene as an effective protecting group

Posted on 13. January, 2014.

Bookmark and Share

The inhibition of glucosidases is one of the most effective therapeutic approaches to treat diseases such as diabetes, cancers, viral infections and Gaucher’s disease. A practical synthesis of neoponkoranol and its related sulfonium salt as potent α‑glucosidase inhibitors has been developed in which the coupling reaction was optimised by using isopropylidene as an effective protecting group. The coupling yields were dramatically improved in this study from 37% to 87%.

A practical synthesis of neoponkoranol and its related sulfonium salt as potent glucosidase inhibitors has been developed in which the key step of coupling reaction was optimised by using isopropylidene as an effective protecting group. The characteristic intramolecular cyclisation of the coupling precursor encountered as side reaction has not been detected previously and coupling yields were dramatically improved in the present study.

Based on their former synthetic studies on a naturally occurring potent α‑glucosidase inhibitor neoponkoranol (7), the authors have developed an efficient strategy to optimise the coupling reaction as the key protocol to synthesise this series of sulfonium salts. Compared with the previously reported route, triflates (19) and (24) selected in the present study as coupling precursors could be more easily and economically prepared from commercially available materials. In addition, coupling yields were dramatically improved from 37% to 87% (in D-mannose derived trial) and from 64% to 85% (in D-glucose derived trial), respectively, indicating that isopropylidene protection of C3 and its adjacent hydroxy group on monosaccharide moiety could effectively prevent the side reaction which was encountered in our previous investigation. It is highly commented that the present findings would greatly facilitate the further structure modification of this group of natural products, which is now underway in their laboratory.

Read the article here, in the December issue of Journal of Chemical Research.

doi: 10.3184/174751913X13823645011477

www.jchemres.co.uk

Click here to subscribe to Journal of Chemical Research.

Click here to follow Journal of Chemical Research on Twitter.