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- Title
Asymmetric Total Synthesis of Mycoleptodiscin A.
- Authors
Zhou, Shupeng; Chen, Hao; Luo, Yijie; Zhang, Wenhao; Li, Ang
- Abstract
The first total synthesis of mycoleptodiscin A, a structurally unusual indolosesquiterpenoid possessing an ortho-benzoquinone motif, has been accomplished. A sulfone alkylation coupled two readily available fragments to give an aryl triene intermediate. The tetracyclic core of the molecule was assembled through a highly enantioselective iridium-catalyzed polyene cyclization. The benzylic homologation was achieved by a cationic cyanation. The indole motif was constructed via a copper-mediated intramolecular CN bond formation at a late stage.
- Subjects
CHEMICAL synthesis; INDOLE compounds; SULFONES synthesis; ARYLATION; CATALYSIS
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 23, p6982
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201501021