Total Synthesis of a New Cytotoxic Acetogenin, Jimenezin, and the Revised Structure
Organic Letters1999Vol. 1(12), pp. 2025–2028
Citations Over Time
Abstract
The first total synthesis of jimenezin was achieved by using carbohydrates as chiral building blocks, thus revising the proposed structure 1 to 2. The key steps in this synthesis include an efficient construction of the THP-THF fragments 3 and 16 through a stereoselective condensation between the pyranyl aldehyde 5 and the acetylene derivative 6, and a palladium-catalyzed coupling reaction of 3 or 16 with a terminal butenolide 4.
Related Papers
- → Design syntheses and mitochondrial complex I inhibitory activity of novel acetogenin mimics(2000)47 cited
- → Mimicry of Annonaceous Acetogenins: Enantioselective Synthesis of a (4R)-Hydroxy Analogue Having Potent Antitumor Activity(2002)36 cited
- → New Type of Mono-tetrahydrofuran Ring Acetogenins from Goniothalamus donnaiensis(1997)36 cited
- → Synthesis and inhibitory activity of ubiquinone–acetogenin hybrid inhibitor with bovine mitochondrial complex I(2003)33 cited
- → Critical role of a methyl group on the γ-lactone ring of annonaceous acetogenins in the potent inhibition of mitochondrial complex I(2013)20 cited