Organic Letters
Organic Letters
5 years ago

Synthesis of (−)-6,7-Dideoxysqualestatin H5 by Carbonyl Ylide Cycloaddition–Rearrangement and Cross-electrophile Coupling

Synthesis of (−)-6,7-Dideoxysqualestatin H5 by Carbonyl Ylide Cycloaddition–Rearrangement and Cross-electrophile Coupling
David M. Hodgson, Younes Fegheh-Hassanpour, Herman O. Sintim, Tanzeel Arif, Hamad H. Al Mamari
An asymmetric synthesis of (−)-6,7-dideoxysqualestatin H5 is reported. Key features of the synthesis include the following: (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 co-generation of keto and diazo functionality through ozonolysis of an unsaturated hydrazone; and (3) stereoretentive Ni-catalyzed Csp3–Csp2 cross-electrophile coupling between tricarboxylate core and unsaturated side chain to complete the natural product.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01513

DOI: 10.1021/acs.orglett.7b01513

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