2022
DOI: 10.1055/a-1941-8680
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Total Synthesis and Anti-inflammatory Activity of Stemoamide-Type Alkaloids Including Totally Substituted Butenolides and Pyrroles

Abstract: The totally substituted butenolide including two tetrasubstituted olefins is a distinct structural motif seen in Stemona alkaloids, but efficient methods for its synthesis are not well developed. As an ongoing program aimed at the collective total synthesis of the stemoamide group, we report a stereodivergent method to give either (E)- or (Z)-totally substituted butenolide from the same intermediate. While the AgOTf-mediated elimination via the E1-type mechanism results in the formation of the kinetic (Z)-tetr… Show more

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Cited by 3 publications
(1 citation statement)
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“…Over the past decade, the direct reductive functionalization of amides to yield amines (Fig. 1a) has emerged as a powerful strategy for total synthesis of alkaloids [26][27][28][29][30][31][32][33][34][35][36][37][38] . Despite the significant progress, the direct catalytic reductive alkylation of amides to yield chiral amines remains a formidable challenge.…”
mentioning
confidence: 99%
“…Over the past decade, the direct reductive functionalization of amides to yield amines (Fig. 1a) has emerged as a powerful strategy for total synthesis of alkaloids [26][27][28][29][30][31][32][33][34][35][36][37][38] . Despite the significant progress, the direct catalytic reductive alkylation of amides to yield chiral amines remains a formidable challenge.…”
mentioning
confidence: 99%