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First Asymmetric Synthesis and Determination of the Absolute Configuration of a Lignan Isolated from Virola sebifera
Author(s) -
Enders Dieter,
Milovanovic Mile,
Voloshina Elena,
Raabe Gerhard,
Fleischhauer Jörg
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400885
Subject(s) - chemistry , enantiopure drug , absolute configuration , nitrile , lignan , enantioselective synthesis , stereochemistry , organic chemistry , stereoselectivity , catalysis
The first asymmetric synthesis of a lignan isolated from the seeds of Virola sebifera , one of the most widely spread Myristicaceae species in Brazil, in four steps (48 % overall yield) and with excellent stereoselectivity ( de , ee ≥ 96 %) is described. The key step is the asymmetric Michael addition of a lithiated enantiopure α‐amino nitrile to an enone, followed by α‐methylation and cleavage of the amino nitrile. The absolute configuration of the naturally occurring 1,4‐diketone was determined by polarimetry as well as by CD spectroscopy and quantum chemical calculations. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)