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- W2067332697 abstract "The total synthesis of the structurally unique secondary metabolite sporolide B (1b) is described. The total synthesis of 1b was developed on the basis of preliminary studies that revealed the reactivity of an appropriate o-quinone as a diene system toward a number of indene derivatives as dienophiles, first in intermolecular and thence intramolecular settings. Thus, substrates were devised (37 and 75) that underwent exquisite intramolecular [4+2] cycloaddition reactions under thermal conditions to provide primitive sporolide-type structures that were subsequently elaborated to a sporolide model system, 9-epi-sporolide B, and 1b. The requisite indene o-quinone precursor 75 was synthesized through a ruthenium-catalyzed [2+2+2] cycloaddition reaction between a propargylic alcohol and a chloroacetylenic cyclopentenyne, followed by elaboration and silver-promoted oxidation of the resulting chloroindene derivative. In addition to the total synthesis of 1b, this work demonstrated, for the first time, the power of the intramolecular hetero [4+2] cycloaddition reaction in the total synthesis of complex molecules and the application of the ruthenium-catalyzed [2+2+2] cycloaddition reaction to highly substituted indene systems possessing a chlorine residue on the aromatic nucleus." @default.
- W2067332697 created "2016-06-24" @default.
- W2067332697 creator A5031990549 @default.
- W2067332697 creator A5042463133 @default.
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- W2067332697 date "2010-07-22" @default.
- W2067332697 modified "2023-10-16" @default.
- W2067332697 title "Total Synthesis of Sporolide B and 9-<i>epi</i>-Sporolide B" @default.
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- W2067332697 doi "https://doi.org/10.1021/ja1048994" @default.
- W2067332697 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/2932487" @default.
- W2067332697 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/20698702" @default.
- W2067332697 hasPublicationYear "2010" @default.
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