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Published on: March 15, 2012
First total synthesis of aspinolide B, a new pentaketide produced by Aspergillus ochraceus
R A Pilli1, M M Victor, A de Meijere
1Instituto de Química, Unicamp, Cx. Postal 6154, 13083-970 Campinas, SP Brazil. pilli@iqm.unicamp.br
Abstract:
The first asymmetric total synthesis of Aspinolide B (1), a new 10-membered lactone discovered by chemical screening methods in the cultures of Aspergillus ochraceus, has been accomplished. The key steps included a selective Felkin-type addition of TMS-acetylene to aldehyde 3a and a Nozaki-Hiyama-Kishi coupling reaction to build the required 10-membered ring. This synthesis confirmed the absolute stereochemistry of aspinolide B, established through Helmchen's method and corrected its previously reported specific optical rotation.
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