Synthesis of (-)-melazolide B, a degraded limonoid, from a natural terpene precursor

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Tetrahedron Chem. 2022 Mar;1:100011. doi: 10.1016/j.tchem.2022.100011. Epub 2022 Mar 22.

ABSTRACT

Degraded limonoids are a subclass of limonoid natural products that derive from ring-intact or ring-rearranged limonoids. Establishment of robust synthetic routes to access them could provide valuable materials to identify the simplest active pharmacophore responsible for the observed biological activities of the parent molecules. This communication delineates the development of a divergent strategy to furnish melazolide B and several other related congeners from a common keto-lactone intermediate, which was rapidly assembled from α-ionone. A chemoselective carbonyl α,β-dehydrogenation and a Wharton reduction were key strategic steps in this synthetic pathway.

PMID:38606284 | PMC:PMC11008529 | DOI:10.1016/j.tchem.2022.100011