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Xuan Zhou, Tao Xiao, Yusuke Iwama and Prof. Dr. Yong Qin Biomimetic Total Synthesis of (+)-Gelsemine Angewandte Chemie International Edition 51

Version of Record online: 4 APR 2012 | DOI: 10.1002/anie.201201736

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Challenging: (+)-gelsemine was synthesized from (R,R)-aziridine 1 in 25 steps with approximately 1 % overall yield. A multistep, one-pot enol–oxonium cyclization cascade was used to construct, simultaneously, the E ring, F ring, C3 stereocenter, and C7 quaternary stereocenter. This synthesis using the enol–oxonium cyclization reaction as a key step to make the cage structure has demonstrated the proposed biosynthetic pathway of the gelsemine family.

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