Journal of Organic Chemistry p. 2235 - 2244 (1992)
Update date:2022-07-31
Topics: Synthesis Oxidation Yield NMR spectroscopy Mass spectrometry HPLC Reduction Enantioselectivity Esterification Lactone Deprotection Protecting group Purification Retrosynthetic analysis Catalysis Macrocyclization Coupling Reaction Chiral synthesis
Boger, Dale L.
Curran, Timothy T.
Full details of a study leading to a synthesis of the optically active C13-C26 lower subunit of rhizoxin including the side-chain chromophore characteristic of the full class of antimitotic agents are described.A key element of the synthesis is the stereoselective introduction of the C18-C19 trisubstituted olefin through use of a Wadsworth-Horner-Emmerson condensation of 3 with β-keto phosphonate 38 bearing resident functionality suitable for the diastereoselective introduction of C15-C17 employing a hydroxyl-directed reduction of the resultant β-hydroxy ketone.
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Doi:10.1021/jo00034a056
(1992)Doi:10.1039/c39920000050
(1992)Doi:10.1039/d0cc07547g
(2021)Doi:10.1021/acs.orglett.0c01747
(2020)Doi:10.1021/jo3016055
(2012)Doi:10.1016/j.ejmech.2015.03.045
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