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Asymmetric Total Synthesis of a Pentacyclic Lycopodium Alkaloid: Huperzine‐Q
Author(s) -
Nakayama Atsushi,
Kogure Noriyuki,
Kitajima Mariko,
Takayama Hiromitsu
Publication year - 2011
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.201103550
Subject(s) - huperzine a , stereocenter , lycopodium , moiety , total synthesis , stereochemistry , claisen rearrangement , stereoselectivity , chemistry , enantioselective synthesis , alkaloid , yield (engineering) , organic chemistry , materials science , enzyme , acetylcholinesterase , metallurgy , catalysis
Right on Q : The first asymmetric total synthesis of (−)‐huperzine‐Q, which possesses six stereogenic centers and a spiroaminal moiety, has been achieved in 19 steps and 16.4 % overall yield. This synthesis involved a novel stereoselective Pauson–Khand reaction, a vinyl Claisen rearrangement, and a biomimetic spiroaminal formation. TBDPS= tert ‐butyldiphenylsilyl.