Journal of Organic Chemistry p. 2235 - 2244 (1992)
Update date:2022-07-31
Topics:
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
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