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Royal Society of Chemistry, Chemical Communications, 63(49), p. 7088, 2013

DOI: 10.1039/c3cc43665a

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Versatile construction of functionalized tropane ring systems based on lactam activation: enantioselective synthesis of (+)-pervilleine B

Journal article published in 2013 by Su-Yu Huang, 王爱娥, 黄培强, Zong Chang, Shi-Chuan Tuo, Long-Hui Gao, Ai-E. Wang, Pei-Qiang Huang ORCID
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

National Basic Research Program (973 Program) of the MOST of China [2010CB833200]; NSF of China [20832005, 21072160]; Program for Changjiang Scholars and Innovative Research Team in University of the MOE, China ; The halo-assisted intramolecular addition of silyl enol ethers with in situ activated lactams yielded (hydroxylated) 1-halo-8-azabicyclo[3,2,1]octane and 1-halo-9-azabicyclo[3,3,1] nonane ring systems, which provided an easy enantioselective access to 6 beta-silyloxytropane-3-one, 3 alpha,6 beta-dihydroxytropane, and pervilleine B. The absolute configuration of the natural (-)-pervilleine B was determined to be 1R,3R,5S,6R.