ol7b01513_si_002.cif (26.74 kB)
Synthesis of (−)-6,7-Dideoxysqualestatin H5 by Carbonyl Ylide Cycloaddition–Rearrangement and Cross-electrophile Coupling
dataset
posted on 2017-06-19, 23:03 authored by Younes Fegheh-Hassanpour, Tanzeel Arif, Herman O. Sintim, Hamad H. Al Mamari, David M. HodgsonAn 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.
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hydrazonediazo functionalityCspfacilitationco-generationcross-electrophileβ- hydroxy -α-ketoester motifRhtartrate acetonide enolateYlideCross-electrophilealkylationsynthesisstereoretentiveoxidationdiastereoselective ntricarboxylate coreylideformationdideoxysqualestatinDideoxysqualestatinKey featuresNi-catalyzedcarbonylentrycyclicCarbonylozonolysiside chainSynthesiCycloaddition
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