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First Synthesis of the Cytotoxic and Antifungal C 14 ‐Amine (2 S ,3 E ,5 Z )‐2‐Amino‐3,5,13‐tetradecatriene Isolated from the New Zealand Ascidian Pseudodistoma novaezelandiae
Author(s) -
Enders Dieter,
Finkam Michael
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199319930190
Subject(s) - stereocenter , chemistry , antifungal , carbamate , yield (engineering) , amine gas treating , enantiomer , nucleophile , stereochemistry , enantioselective synthesis , medicinal chemistry , combinatorial chemistry , organic chemistry , microbiology and biotechnology , catalysis , materials science , metallurgy , biology
The synthesis of (2 S ,3 E ,5 Z )‐2‐amino‐3,5,13‐tetradecatriene [( S ‐ 1 )] with high enantiomeric purity in excellent overall yield is described. In the crucial step the stereogenic center was generated by nucleophilic addition of tert ‐butyl carbamate to a planar‐chiral tetracarbonyliron(1 +) complex.