Thursday, May 22, 2014
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Total synthesis of polyene
compounds with N-methyliminodiacetic acid (MIDA) boronate building
A method for total
synthesis of polyene natural products could be useful for exploring their
therapeutic applications. Analysis of a natural product database showed that
over 75% of polyene compounds contain no more than 12 different polyene
motifs. A two-step iterative coupling reaction used MIDA boronate analogs of
polyene motifs to generate polyene chains up to
20 carbons long and utilized additional MIDA boronate analogs to add desired
structures to the chain termini. Total synthesis with the method yielded
milligram quantities of the antimicrobial and anticancer compound asnipyrone B and two other natural
products. Next steps include automating the method and extending it to other
classes of small molecules.
Published online May 22, 2014
Unpatented; licensing status
Woerly, E.M. et al. Nat.
Chem.; published online May 11, 2014;
Contact: Martin D. Burke, University of Illinois at
Urbana-Champaign, Urbana, Ill.
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