American Chemical Society
np7b00706_si_002.cif (1.2 MB)

Halogenated C15 Acetogenin Analogues of Obtusallene III from a Laurenciella sp. Collected in Corsica

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posted on 2018-01-30, 17:55 authored by Sylvain Sutour, Bruno Therrien, Stephan H. von Reuss, Félix Tomi
NMR chemical profiling of a Laurenciella sp. using a computerized method developed in our laboratory resulted in the identification of five new compounds (15) and 17 known compounds, among which 3-(E)-laurenyne represented by far the most abundant metabolite. Compounds 1 to 5 were isolated and fully characterized by detailed spectroscopic analysis. The absolute configuration and structural features of compound 1 were determined by single-crystal X-ray diffraction analysis. Compounds 1 to 4 are 12-membered cyclic ether acetogenins that are present in solution as interconverting conformers exhibiting an (aR) configuration of the bromoallene unit together with an S configuration at C-4. Among these, compound 3 is the first obtusallene derivative with bromine substituents at both the C-7 and C-12 positions. Compound 5 is an acetogenin bearing a [5.5.1]­bicyclotridecane ring system. A plausible biosynthetic route to 14 is proposed.