Total synthesis of herbimycin A
Kendra D Carter1, James S Panek
1Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
Organic Letters
|January 3, 2004
Abstract:
[structure: see text] Herbimycin A (HA) belongs to a class of antibiotics known as the benzoquinoid ansamycins. Members of this class have shown promising biological activity as Hsp90 inhibitors. An enantioselective synthesis of HA is described, employing asymmetric syn-crotylation methodology to introduce the C10, C11, C14, and C15 stereocenters. The C6-C7 stereocenters were introduced using Brown's alpha-pinene-derived gamma-methoxy allylborane reagent. The C12 stereocenter was established by diastereoselective hydroboration.
