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• W2147174016 abstract "The total synthesis of the biologically active marine natural product leucascandrolide A is reported. A convergent strategy is employed, allowing for the rapid assembly of the macrolide moiety. Key steps of our approach include the diastereoselective addition of a zinc alkynilide to (R)-isopropylidene glyceraldehyde, the enantioselective copper(I) fluoride catalyzed aldol addition of a TMS-dienolate to crotonaldehyde, and the formation of a 2,6-trans-substituted tetrahydropyran by selenium-mediated intramolecular cyclization. Moreover, dramatic solvent effects observed in the macrolactonization reaction suggest that hydrogen-bonding effects play a critical role. An improved route to a key intermediate of our synthesis is documented." @default.
• W2147174016 created "2016-06-24" @default.
• W2147174016 creator A5049997686 @default.
• W2147174016 creator A5053542178 @default.
• W2147174016 date "2003-10-31" @default.
• W2147174016 modified "2023-10-16" @default.
• W2147174016 title "Leucascandrolide A: Synthesis and Related Studies" @default.
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• W2147174016 doi "https://doi.org/10.1021/jo034964v" @default.
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