Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 8, Pages 2115-2119Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201711603
Keywords
asymmetric synthesis; Bronsted acid; polyene cyclizations; terpenes; total synthesis
Categories
Funding
- National Natural Science Foundation of China [21462023, 21778025]
- Natural Science Foundation of Jiangxi Province [20143ACB20007]
- Education Department of Jiangxi Province [150297]
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The first enantioselective polyene cyclization initiated by a BINOL-derived chiral N-phosphoramide (NPA) catalyzed protonation of an imine is described. The ion-pair formed between the iminium ion and chiral counter anion of the NPA plays an important role for controlling the stereochemistry of the overall transformation. This strategy offers a highly efficient approach to fused tricyclic frameworks containing three contiguous stereocenters, which are widely found in natural products. In addition, the first catalytic asymmetric total synthesis of (-)-ferruginol was accomplished with an NPA catalyzed enantioselective polyene cyclization, as the key step for the construction of the tricyclic core, with excellent yield and enantioselectivity.
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