Journal
TETRAHEDRON LETTERS
Volume 56, Issue 23, Pages 3165-3168Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2014.12.089
Keywords
Gelsemine; Alkaloid; Total synthesis; Pericyclic cascade; Zincke aldehyde
Categories
Funding
- Direct For Mathematical & Physical Scien [1262040] Funding Source: National Science Foundation
- Division Of Chemistry [1262040] Funding Source: National Science Foundation
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We have developed a Zincke-aldehyde-based approach to the complex alkaloid gelsemine. It features a key thermal pericyclic cascade that converts a Zincke aldehyde bearing a pendant alkene into a hydroiso-indolone product that shares many structural features with the target molecule. Our efforts to convert these intermediates to gelsemine are also discussed. (C) 2014 Elsevier Ltd. All rights reserved.
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