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Enantioselective total synthesis of harmonine, a defence alkaloid of ladybugs (Coleoptera: Coccinellidae)
Author(s) -
Enders Dieter,
Bartzen Dominika
Publication year - 1991
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.1991199101103
Subject(s) - enantioselective synthesis , stereocenter , chemistry , stereochemistry , total synthesis , coccinellidae , methyllithium , nucleophilic addition , alkaloid , aldehyde , organic chemistry , biology , predator , ecology , catalysis , predation
An efficient and highly enantioselective (ee > 97%) total synthesis of the ladybug defence alkaloid (17 R ,9 Z )‐1,17‐diaminooctadec‐9‐ene [( R,Z )‐1, harmonine] in good overall yield is described. As the key step for the generation of the stereogenic center, asymmetric CC bond formation by nucleophilic addition of methyllithium to an aldehyde SAMP hydrazone is used.