Synthesis of (−)-6,7-Dideoxysqualestatin H5
by Carbonyl Ylide Cycloaddition–Rearrangement and Cross-electrophile
Coupling
Version 3 2017-07-07, 04:43
Version 2 2017-06-26, 18:41
Version 1 2017-06-19, 23:03
Posted on 2017-07-07 - 04:43
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.
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Fegheh-Hassanpour, Younes; Arif, Tanzeel; Sintim, Herman O.; Al Mamari, Hamad H.; Hodgson, David M. (2017). Synthesis of (−)-6,7-Dideoxysqualestatin H5
by Carbonyl Ylide Cycloaddition–Rearrangement and Cross-electrophile
Coupling. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b01513
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AUTHORS (5)
YF
Younes Fegheh-Hassanpour
TA
Tanzeel Arif
HS
Herman O. Sintim
HA
Hamad H. Al Mamari
DH
David M. Hodgson
KEYWORDS
hydrazonediazo functionalityCspfacilitationco-generationcross-electrophileβ- hydroxy -α-ketoester motifRhtartrate acetonide enolateYlideCross-electrophilealkylationsynthesisstereoretentiveoxidationdiastereoselective ntricarboxylate coreylideformationdideoxysqualestatinDideoxysqualestatinKey featuresNi-catalyzedcarbonylentrycyclicCarbonylozonolysiside chainSynthesiCycloaddition