First total synthesis of Aspinolide B, a new pentaketide produced by Aspergillus ochraceus

The first asymmetric total synthesis of Aspinolide B (1), a new 10-membered lactone discovered by chemical screening methods in the cultures of Asperg illus ochraceus, has been accomplished. The key steps included a selective Felkin-type addition of TMS-acetylene to aldehyde 3a and a Nozaki-Hiyama-Ki shi coupling reaction to build the required 10-membered ring. This synthesi s confirmed the absolute stereochemistry of aspinolide B, established throu gh Helmchen's method and corrected its previously reported specific optical rotation.