Total synthesis of dihydrolysergic acid and dihydrolysergol: development of a divergent synthetic strategy applicable to rapid assembly of D-ring analogs.

  title={Total synthesis of dihydrolysergic acid and dihydrolysergol: development of a divergent synthetic strategy applicable to rapid assembly of D-ring analogs.},
  author={Kiyoun Lee and Yam B. Poudel and Christopher M. Glinkerman and Dale L. Boger},
  volume={71 35},
The total syntheses of dihydrolysergic acid and dihydrolysergol are detailed based on a Pd(0)-catalyzed intramolecular Larock indole cyclization for the preparation of the embedded tricyclic indole (ABC ring system) and a subsequent powerful inverse electron demand Diels-Alder reaction of 5-carbomethoxy-1,2,3-triazine with a ketone-derived enamine for the introduction of a functionalized pyridine, serving as the precursor for a remarkably diastereoselective reduction to the N-methylpiperidine D… Expand
18 Citations
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The enantioselective synthesis of (+)-lysergol was completed in 12 steps and an overall yield of 13% starting from a known literature precursor. The key step relies on a domino reaction containing aExpand
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The synthesis, characterization, and a study of the cycloaddition reactions of 5-nitro-1,2,3-triazine are reported, revealing a remarkable reaction rate and efficiency. Expand
Synthesis of (+)-Lysergol and Its Analogues To Assess Serotonin Receptor Activity.
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Abstract A novel free radical cyclisation approach for the synthesis of lysergic acid analogues has been investigated. The homolytic cleavage of carbon-bromine bond, mediated by tri-n-butyltinExpand
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Asymmetric formal synthesis of (+)-lysergic acid was achieved with a reductive ring-opening reaction of chiral 2-alkynyl-3-indolyloxirane with NaBH(3)CN as the key step to construct the ergot alkaloid core structure. Expand
Total synthesis of (+)-lysergic acid.
We report the enantioselective total synthesis of (+)-lysergic acid using two different strategies, which featured three metal-catalyzed reactions for the construction of the BCD three rings,Expand
Asymmetric total synthesis of ent-(-)-roseophilin: assignment of absolute configuration.
  • D. Boger, J. Hong
  • Chemistry, Medicine
  • Journal of the American Chemical Society
  • 2001
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The quest for new mild and selective modifications of natural structures: laccase-catalysed oxidation of ergot alkaloids leads to unexpected stereoselective C-4 hydroxylation.
Laccase-catalysed oxidation of ergot alkaloids in the absence of chemical mediators allowed the unexpected isolation of the mono-hydroxylated derivatives of compounds 2-7, and allowed, for the first time, functionalisation at the C-4 position of the ergoline skeleton. Expand
Total Syntheses of (−)-Pyrimidoblamic Acid and P-3A
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The first total syntheses of lysergine and setoclavine are described, as well as a new and efficient synthesis of lysergic acid. The starting material for these syntheses is tryptophan, protected asExpand