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Total Syntheses of Lycopodium Alkaloids (+)‐Fawcettimine, (+)‐Fawcettidine, and (−)‐8‐Deoxyserratinine
Author(s) -
Li Houhua,
Wang Xiaoming,
Lei Xiaoguang
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201106753
Subject(s) - lycopodium , total synthesis , stereochemistry , pinacol , chemistry , organic chemistry , catalysis
A shared story : Three fawcettimine‐ and serratinine‐type Lycopodium alkaloids are prepared from a common tetracyclic spirodiketone intermediate in concise total syntheses (see scheme). The intermediate was constructed by a remarkable biosynthesis‐inspired transannular NC bond formation to the spiro‐configured carbon center and a hydroxy‐directed pinacol coupling promoted by SmI 2 .