Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 11, Issue 22, Pages 6601-6608Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200500417
Keywords
aldol reaction; enantioselectivity; octalactin A; rapid lactonization; total synthesis
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Octalactin A, an antitumor agent containing an eight-membered lactone moiety, has been stereoselectively prepared by means of enantioselective aldol reactions of selected silyl enolates with achiral aldehydes, promoted by a chiral Sn-II complex. The medium-sized lactone part was effectively constructed by way of a new and rapid mixed-anhydride lactonization using 2-methyl-6-nitrobenzoic anhydride (MNBA) with a catalytic amount of 4- (dimethylamino)pyridine (DMAP) or 4-(dimethylamino)pyridine I-oxide (DMAPO). The use of only 5 mol % of DMAP or 2 mol % of DMAPO rapidly promoted formation of the medium-sized ring of the octalactin, demonstrating the remarkable efficiency of the new lactonization protocol.
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