Liebigs Annalen der Chemie

Enantioselective total synthesis of harmonine, a defence alkaloid of ladybugs (Coleoptera: Coccinellidae)

D Enders, D Bartzen

Index: Enders, Dieter; Bartzen, Dominika Liebigs Annalen der Chemie, 1991 , # 6 p. 569 - 574

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Citation Number: 25

Abstract

Abstract An efficient and highly enantioselective (ee> 97%) total synthesis of the ladybug defence alkaloid (17R, 9Z)-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 C [BOND] C bond formation by nucleophilic addition of methyllithium to an aldehyde SAMP hydrazone is used.