Characterization

and, Bodo Zibrowius; Löffler, Elke

doi:10.1002/9783527618286.ch18e

Cited by 2 publications

(1 citation statement)

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“…Moreover, one minor terpenoids, 10,llepoxycaulerpenyne, was observed to induce a dramatic proliferation of Nicotiana gluuca callus cultures, which can be taken as a model for marine angiosperms [S]. While any direct risk for human health has not clearly emerged to date, these phenomena rank that of Mediterranean-adapted C. taxifolia to a case of biological pollution whose consequences, in synergism with other introduced species [6], are difficult to foresee for both the Mediterranean Sea and, on possible natal homing of this algal strain, also the tropics [7].…”

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confidence: 99%

ChemInform Abstract: Caulerpenyne‐Amine Reacting System as a Model for in vivo Interactions of Ecotoxicologically Relevant Sesquiterpenoids of the Mediterranean‐ Adapted Tropical Green Seaweed Caulerpa taxifolia.

et al. 1996

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Caulerpenyne (l), the most abundant of the ecotoxicologically relevant sesquiterpenoids of the Mediterranean-adapted tropical green seaweed Caulerpa taxzfolia, was found to react with Et,N or pyridine in MeOH by initial deprotection o f C(1)HO to give oxytoxin 1 (Za), previously isolated from the sacoglossan mollusc Oxynoe olivacea. With BuNH,, without any precaution to exclude light, 1 gave the series of racemic 3 and 4, and achirdl (4E,6E)-5, (4&62)-5, (4Z,6E)-5, and (42,62)-5 pyrrole compounds, corresponding to formal C(4) substitution, 4S-D -elimination, and (E/Z)-isomerization at the C(4)=C(5) and C(6)=C(7) bonds. Changing to CDCl, as solvent in the dark, 1 gave cleanly, via 2a as an intermediate, 3 and (4E,6E)-5. The latter proved to be prone to (E/Z)-photoisomerization. Under standard acetylation conditions, 3 gave (4E,6E)-5 via acetamide 7 as an intermediate. Particular notice is warranted by selective deprotection of 1 at C(1), mimicking enzyme reactions, and unprecedented formation of pyrrole compounds from freely-rotating, protected 1,Cdialdehyde systems.

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confidence: 99%