Selective synthesis of the para-quinone region of geldanamycin.
[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.
Andrus
Merritt B
MB
Department of Chemistry and Biochemistry, Brigham Young University, C100 BNSN, Provo, Utah 84602-5700, USA. mbandrus@chem.byu.edu
Hicken
Erik J
EJ
Meredith
Erik L
EL
Simmons
Bryon L
BL
Cannon
John F
JF
D016227:Benzoquinones; D047029:Lactams, Macrocyclic; D008956:Models, Chemical; D015394:Molecular Structure; D011809:Quinones / Q000138:chemical synthesis*
D016227:Benzoquinones; D047029:Lactams, Macrocyclic; D011809:Quinones; C001277:geldanamycin