Total Synthesis of (-)-Spiroleucettadine
Journal Title
Angew Chem Int Ed Engl
Publication Type
Journal Article
Abstract
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.
Publisher
Wiley
Keywords
Natural Products; Total synthesis; hypervalent iodine; oxidation reaction
PubMed ID
28960638
NHMRC Grants
NHMRC/1117089
Rights Notice
Refer to copyright notice on published article.


Creation Date: 2017-10-02 09:52:31
Last Modified: 2017-10-16 02:08:04
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