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- W3034074246 abstract "The highs, lows, and diversions of a journey leading to two syntheses of 6,7-dideoxysqualestatin H5 is described. Both syntheses relied on highly diastereoselective n-alkylations of a tartrate acetonide enolate and subsequent oxidation–hydrolysis to provide an asymmetric entry to β-hydroxy-α-ketoester motifs. The latter were differentially elaborated to diazoketones which underwent stereo- and regioselective Rh(II)-catalysed cyclic carbonyl ylide formation–cycloaddition and then acid-catalysed transketalisation to generate the 2,8-dioxabicyclo[3.2.1]octane core of the squalestatins/zaragozic acids at the correct tricarboxylate oxidation level. The unsaturated side chain was either protected with a bromide substituent during the transketalisation or introduced afterwards by a stereoretentive Ni-catalyzed Csp3–Csp2 cross-electrophile coupling. 1 Introduction 2 Racemic Model Studies to the Squalestatin/Zaragozic Acid Core 3 Asymmetric Model Studies to a Keto α-Diazoester 3.1 Dialkyl Squarate Desymmetrisation 3.2 Tartrate Alkylation 3.2.1 Further Studies on Seebach’s Alkylation Chemistry 4 Failure at the Penultimate Step to DDSQ 5 Second-Generation Approach to DDSQ: A Bromide Substituent Strategy 5.1 Stereoselective Routes to E-Alkenyl Halides via β-Oxido Phosphonium Ylides 5.2 Back to DDSQ Synthesis 6 An Alternative Strategy to DDSQ: By Cross-Electrophile Coupling 7 Alkene Ozonolysis in the Presence of Diazo Functionality: Accessing α-Ketoester Intermediates 8 Summary" @default.
- W3034074246 created "2020-06-12" @default.
- W3034074246 creator A5050035899 @default.
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- W3034074246 date "2020-06-04" @default.
- W3034074246 modified "2023-10-18" @default.
- W3034074246 title "Evolution of a Cycloaddition–Rearrangement Approach to the Squalestatins: A Quarter-Century Odyssey" @default.
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- W3034074246 doi "https://doi.org/10.1055/s-0040-1707127" @default.
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