Synthesis and Absolute Configuration of Hyperaspine, an Alkaloid of the Ladybird Hyperaspis campestris

European Journal of Organic Chemistry
2005.0

Abstract

Hyperaspine (1a), isolated from the European Coccinellidae Hyperaspis campestris, is the first representative of a new type of ladybird alkaloids having a 3-oxaquinolizidine skeleton. A new total synthesis of (+/-)-hyperaspine starting from protected piperidin-4-one has been achieved. The absolute configuration of the natural alkaloid was unequivocally established to be 3S,4aS,6R,8S by HPLC analyses on a chiral column. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).

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