期刊
TETRAHEDRON LETTERS
卷 60, 期 14, 页码 979-982出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2019.03.004
关键词
beta-Carboline; Ring closing metathesis; Fischer indole synthesis; Chiral pool
资金
- NIH [GM065503]
- Robert A. Welch Foundation [Y-1362]
- NSF [CHE-0234811, CHE-0840509]
Asymmetric total synthesis of the imidazole containing beta-carboline natural product, haploscleridamine, from histidine is described. Key to the successful assembly of this alkaloid is a ring-closing metathesis reaction of an imidazole derived allylic alcohol to construct a 3-piperidinone. Application of the Buchwald-modification of the classical Fischer indolization and deprotection of the N-tosyl moiety delivered haploscleridamine. (C) 2019 Published by Elsevier Ltd.
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