Date of Award
Maurice H. Maxwell, Jr. Ph.D.
A new enantioselective convergant approach to Retigeranic acid (1) using (2+3} cyclopentene annulation methodology was used. A vinyl cyclopropane (8) intermediate was formed from the enone (9) and the bromoester (10). This product (8) was then pyrolized to yield the triquinane ring system (7). The pyrolysis product was reduced and saponified to give one enatiomer of Retigeranic acid (1) in good yield.
Bryant, Teresa L., "ENANTIOSELECTIVE SYNTHESIS OF (-)-RETIGERANIC ACID" (1988). Theses, Dissertations & Honors Papers. 321.