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Asymmetric total synthesis of mycoleptodiscin A

Shupeng Zhou¹, Hao Chen¹, Yijie Luo¹

¹State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China) http://angligroup.sioc.ac.cn.

Angewandte Chemie (International Ed. in English)

|April 25, 2015

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 C-N bond formation at a late stage.

Keywords:

CN bond formation allylic substitution indole terpenoids iridium catalysis polyene cyclization

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