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Heterolignans: Stereoselective Synthesis of an 11‐Amino Analog of Azaelliptitoxin
Author(s) -
Routier Julie,
Calancea Mihaela,
David Marion,
Vallée Yannick,
Denis JeanNoël
Publication year - 2008
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.200800880
Subject(s) - enantiopure drug , stereocenter , chemistry , glycidol , stereoselectivity , aldehyde , stereochemistry , yield (engineering) , amino acid , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , biochemistry , materials science , metallurgy
The 11‐amino‐azaelliptitoxin analog (11 R ,11a S ,5 R )‐ 15 has been prepared stereoselectively in eight steps and 24 % overall yield from commercially available ( S )‐glycidol ( 7 ) via the original enantiopure chiral α‐amino aldehyde 9 , used as chiral precursor for the creation of the two other stereogenic centers of the target framework. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)