Asymmetric Total Synthesis of a Pentacyclic  Lycopodium  Alkaloid: Huperzine‐Q | Zendy

Nakayama Atsushi | Zendy; Kogure Noriyuki | Zendy; Kitajima Mariko | Zendy; Takayama Hiromitsu | Zendy

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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.

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