Journal
TETRAHEDRON
Volume 74, Issue 11, Pages 1129-1134Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2018.01.034
Keywords
Akuammiline aklaloids; Strictamine; Total synthesis; Johnson-Claisen rearrangement
Categories
Funding
- National Natural Science Foundation of China [201702005]
- excellent young scientist foundation of Sichuan University [2016SCU04A10]
- Chongqing Science & Technology Commission Project [cstc2016jcyjA0168]
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An asymmetric total synthesis of the akuammiline alkaloid (+)-strictamine is described. The key steps of the synthetic route involve an improved Johnson-Claisen rearrangement to facilitate the formation of the challenging C15-C20 linkage and the (E)-alkene side chain, intramolecular nucleophilic substitution cyclization to establish the E ring and diastereoselective Brown hydroboration of the terminal alkene to introduce the C16 stereocenter. (C) 2018 Elsevier Ltd. All rights reserved.
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