Journal
TETRAHEDRON
Volume 71, Issue 35, Pages 5897-5905Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2015.05.093
Keywords
1,2,3-Triazine cycloaddition; Ergot alkaloids; Palladium catalyzed indole synthesis; Diels-Alder cycloaddition
Categories
Funding
- National Institutes of Health [CA042056, CA041101]
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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-ring. By design, the use of the same ketone-derived enamine and a set of related complementary heterocyclic azadiene [4+2] cycloaddition reactions permitted the late stage divergent preparation of a series of alternative heterocyclic derivatives not readily accessible by more conventional approaches. (C) 2015 Elsevier Ltd. All rights reserved.
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