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A concise and divergent approach to radicamine B and hyacinthacine A(3) based on a step-economic transformation

Journal article published in 2012 by Jin-Cheng Liao, 黄培强, Kai-Jiong Xiao ORCID, Xiao Zheng, Pei-Qiang Huang ORCID
This paper was not found in any repository; the policy of its publisher is unknown or unclear.
This paper was not found in any repository; the policy of its publisher is unknown or unclear.

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Abstract

Based on our recently developed step-economic methodology of reductive alkylation of lactams/amides, we have developed a two-step synthesis of azasugar radicamine B (2a) and a four-step synthesis of azasugar hyacinthacine A(3) (5) from the common chiral building block 12. Hantzsch ester (HEH) was used as a milder hydride donor in the one-pot stereoselective reductive alkylation of lactam 12. The Wacker oxidation of fully substituted pyrrolidine derivative 2,5-trans-17 led to the synthesis of hyacinthacine A(3) (5). Compound 2,5-trans-17 could also serve as a plausible key intermediate for the synthesis of broussonetine sub-class of azasugars. (C) 2012 Elsevier Ltd. All rights reserved. ; National Basic Research Program (973) of China [2010CB833200]; NSF of China [20832005, 21072160]; Fundamental Research Funds for the Central Universities of China [201112G001]; Ministry of Education of China