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Updated: Aug 30, 2026
A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
Selective synthesis of the para-quinone region of geldanamycin
Merritt B Andrus1, Erik J Hicken, Erik L Meredith
1Department of Chemistry and Biochemistry, Brigham Young University, C100 BNSN, Provo, Utah 84602-5700, USA. mbandrus@chem.byu.edu
Abstract:
[structure: see text] The quinone portion of the ansamycin geldanamycin was made with complete selectivity from the 1,4-dihydroquinone generated from a 1,4-bis-methoxymethyl (MOM) ether intermediate. Palladium catalysis with air gave the desired product in 98% isolated yield. The structure was established using NMR, UV, and X-ray analysis with comparisons to geldanamycin, ortho-quino-geldanamycin and a model compound.
