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- Title
Total Synthesis of (−)-Spiroleucettadine.
- Authors
Lamb, Richard A.; Aberle, Nicholas S.; Lucas, Nigel T.; Lessene, Guillaume; Hawkins, Bill C.
- Abstract
One of a number of intriguing new alkaloids isolated from the Leucetta sp. sponge in 2004, spiroleucettadine displayed unique structural features on a restricted scaffold: a trans-fused 5,5-bicyclic ring system together with an amino hemiketal moiety. Attempts to synthesize the initially proposed structure failed, raising questions as to its veracity, and structure revision ensued in 2008; no successful synthetic approach has been reported to date. Herein, we describe the enantiospecific total synthesis of (−)-spiroleucettadine by a highly efficient biomimetic approach starting from l-tyrosine. One of two key hypervalent-iodine-mediated oxidation reactions forged the spirocyclic center, and the other enabled the installation of the methylamine side chain in the penultimate step. Our approach provides synthetic access to a new class of spiroannulated natural products and will enable future studies of the structure-biological-activity relationships of these antibacterial compounds.
- Subjects
SPIRO compounds synthesis; RING formation (Chemistry); CRYSTAL structure; STRUCTURE-activity relationships; ANTIBACTERIAL agents
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 46, p14855
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201708110