Total Synthesis of (-)-Spiroleucettadine
- Journal Title
- Angew Chem Int Ed Engl
- Publication Type
- Journal Article
- Amongst an intriguing number of new alkaloids isolated from the Leucetta sp. sponge in 2004 was spiroleucettadine, which displayed unique structural features on a restricted scaffold: a trans-fused 5,5-bicyclic ring system together with an amino-hemiketal moiety. Attempts at synthesizing the initially proposed structure failed raising questions as to its veracity and as a result structure revision ensued in 2008; no successful synthetic approach has been reported to date. Herein, we describe the first enantiospecific total synthesis of (-)-spiroleucettadine using a highly efficient biomimetic approach starting from L-tyrosine. The key steps in the synthesis include two hypervalent iodine mediated oxidations: one forges the spirocyclic centre, while the other, in the penultimate step, allows for the installation of the methylamine side chain. Our work provides synthetic entry into a new class of spiro-annulated natural products.
- Natural Products; Total synthesis; hypervalent iodine; oxidation reaction
- PubMed ID
- Publisher's Version
- NHMRC Grants
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- Refer to copyright notice on published article.
Creation Date: 2017-10-02 09:52:31Last Modified: 2017-10-16 02:08:04