Synthesis of (−)-6,7-dideoxysqualestatin H5 by carbonyl ylide cycloaddition–rearrangement and cross-electrophile coupling
An asymmetric synthesis of (−)-6,7-dideoxysqualestatin H5 is reported. Key features of the synthesis include: (1) highly diastereoselective n-alkylation of a tartrate acetonide enolate and subsequent oxidation−hydrolysis to provide an asymmetric entry to a β-hydroxy-α-ketoester motif; (2) facilitati...
| Váldodahkkit: | , , , , |
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| Materiálatiipa: | Journal article |
| Almmustuhtton: |
American Chemical Society
2017
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| Čoahkkáigeassu: | An asymmetric synthesis of (−)-6,7-dideoxysqualestatin H5 is reported. Key features of the synthesis include: (1) highly diastereoselective n-alkylation of a tartrate acetonide enolate and subsequent oxidation−hydrolysis to provide an asymmetric entry to a β-hydroxy-α-ketoester motif; (2) facilitation of Rh(II)-catalyzed cyclic carbonyl ylide formation−cycloaddition by cogeneration of keto and diazo functionality through ozonolysis of an unsaturated hydrazone; and (3) stereoretentive Ni-catalyzed Csp<sup>3</sup>−Csp<sup>2</sup> cross-electrophile coupling between tricarboxylate core and unsaturated side-chain to complete the natural product. |
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