A biomimetic synthesis of koumine

Abstract

LiAlH4 reduction of natural vobasine (I) followed by SeO2/H2O2 oxidation in dilute sulfuric acid results in the formation of koumine (II) via simultaneous rearrangement of the ethylidene side chain and the indole chromophore. The success of this biomimetic partial synthesis not only confirms the structure of II but also further establishes its absolute configuration through its configuration correlation with I, dregamine and L-(-)-tryptophan. It also reveals the probable biogenetic link between koumine, koumidine (16-epi-normacusine B) and vobasine.

Key words: ALKALOID, GELSEMIUM ELEGANS, CLUSTER COMPOUND, BIONICS, KOUMINE, SARPAGINE ALKALOID, BIOGENETIC SYNTHESIS

CLC Number:

O629

Cite this article

LIU ZHUJIN;YU QIANSHENG. A biomimetic synthesis of koumine[J]. Acta Chimica Sinica, 1987, 45(4): 359-364.

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