Studies on the syntheses of benzoquinone ansamycin antibiotics. Syntheses of the C5-C15 subunits of macbecin I, geldanamycin, and herbimycin A.
[reaction: see text] A general and convergent route to the C(5)-C(15) subunits of the benzoquinone ansamycin antibiotics macbecin I, geldanamycin, and herbimycin A is described. Each subunit is prepared by the stepwise coupling of differentially functionalized aldehydes with a pentenyl dianion equivalent derived from diastereoselective pentynylation and regioselective reductive coupling.
Belardi
Justin K
JK
Department of Chemistry, Yale University, New Haven, Connecticut 06520-8107, USA.
Micalizio
Glenn C
GC
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D016227:Benzoquinones / Q000138:chemical synthesis* / Q000737:chemistry*; D047029:Lactams, Macrocyclic / Q000138:chemical synthesis*; D015394:Molecular Structure; D017828:Rifabutin / Q000031:analogs & derivatives; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D016227:Benzoquinones; D047029:Lactams, Macrocyclic; D017828:Rifabutin; C004532:quinone; C020754:herbimycin; C025514:macbecin I; C001277:geldanamycin