Synthesis of ent-ambrox® from (−)-nidorellol

Using ozonolysis of the acid-catalyzed cyclized products of (−)-nidorellol and air-autoxidation as the key steps, (+)-ambrox was obtained in 53% overall yield. In the course of our synthesis, we discovered that (−)-nidorellol provided (+)-ambrox instead of the expected product, (−)-ambrox. Thus the absolute configuration of (−)-nidorellol was proved to be trans-(5R∗,7R∗,8R∗,9S∗,10R∗)-labda-12,14-diene-7α,8β-diol, which is opposite to that illustrated in a previous report.

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