ORGN 653 |
| A one-pot catalytic aromatic C–H borylation/amidation/oxidation serves as a key reaction in our synthetic approach to autolytimycin. This natural product exhibits anti-tumor properties as a small-molecule inhibitor of the Hsp90 protein chaperone complex. Among its distinct structural features is a 1,3,5-N,O,C trisubstituted arene core. Rapid assembly of this aromatic moiety was made possible by employment of a sterically driven, regioselective Ir-catalyzed aromatic C–H borylation of 3-bromochlorobenzene, followed by an in situ Pd-catalyzed amidation and then an oxidation. A planned Suzuki coupling on the resultant highly functionalized chloroarene would set the stage for a ring-closure metathesis to furnish the macrocyclic ring.
|
|
Total Synthesis of Complex Molecules
8:00 AM-12:00 PM, Wednesday, 13 September 2006 Moscone Center -- Room 132, Oral
Division of Organic Chemistry |
