A new complex iridoid, prismatomerin (1), has been isolated from the leaves of Prismatomeris tetrandra, together with the known glucoside gaertneroside (4). The structures of 1 and 4 were determined by spectroscopic analysis, notably 2D NMR techniques. The (1R,5S,8S,9S,10S)-(-) absolute configuration of prismatomerin (1) was determined by comparison of the vibrational circular dichroism (VCD) spectrum calculated using density functional theory and the experimental VCD spectrum of the O-acetyl derivative 3. Prismatomerin (1) showed remarkable antitumor activity and also interfered with mitotic spindle formation.

Thirteen new metabolites, namely oblongolides B–M (2–13) and 4‐[5‐(1‐hydroxyethyl)furan‐2‐yl]‐4‐oxobutanoic acid (14), together with the six known compounds phomopsolide B (15), alternariol dimethyl ether (16), alternariol monomethyl ether (17), the mycotoxin alternariol (18), ergosterol (19), and 5α,8α‐epidioxyergosterol (20) were isolated from the endophytic fungus Phomopsis sp. The new biologically active norsesquiterpene γ‐lactones differ in their degree of substitution, saturation, and substituent pattern from the known oblongolide 1. Their structures were determined by means of spectroscopic data including HREIMS, 1H NMR, 13C NMR, 2D NMR (HMQC, HMBC, NOESY) and X‐ray single crystal analysis. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Six new metabolites, phomosines D–G (4–7), 6‐hydroxy‐6‐isopropylcyclohex‐1‐enecarboxylic acid (8) and(1aS,3R,4R,4aR,6S,7R,8aS)‐7‐chloro‐3,6‐dihydroxy‐3,4a,8,8‐tetramethyl‐octahydro‐1aH‐naphtho[1‐b]oxirene‐4‐carboxylic acid (9) were isolated together with seven known compounds (1–3, 10–13) from the endophytic fungus Phomopsis sp. The structures of 1–13 were determined by spectroscopic methods (mainly extensive 1D and 2D NMR experiments and by mass spectrometric measurements). The antibacterial, fungicidal, and herbicidal properties of the new compounds were evaluated. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Keywords: 1,6-Anhydro sugars / Chiral building blocks / Branched sugars / Č erný epoxide / Gilman cuprates / Epoxide rearrangement / Vinyl tosylate cross couplingThe alkylated allyl alcohols 6a, 7, and 8 (R = Me, Et, nBu) were formed in the reaction of the Č erný epoxide 3 with the Cyano-Gilman cuprates. The one-pot reaction was initiated by base-catalyzed epoxide allyl alcohol rearrangement to compound 5, followed by unprecedented vinyl tosylate crosscoupling with the cuprates, to form the alkylation products 6a, 7, and 8. The allyl alcohol 6a was transformed into a

Terpenes U 0200 Active Secondary Metabolites from Fungi. Part 22. New Oblongolides Isolated from the Endophytic Fungus Phomopsis sp. from Melilotus dentata from the Shores of the Baltic Sea. -Thirteen new oblongolides B-M, exemplified by oblongolide G (I), K (II), and M (III), are isolated from the title fungus. All new norsesquiterpenes exhibit herbicidal, antifungal, and antibacterial activities. -(DAI, J.; KROHN*, K.; GEHLE, D.; KOCK, I.; FLOERKE, U.; AUST, H.-J.; DRAEGER, S.; SCHULZ, B.; RHEINHEIMER, J.; Eur.

Biologically Active Metabolites from Fungi. Part 23. Novel Highly Substituted Biaryl Ethers, Phomosines D-G, Isolated from the Endophytic Fungus Phomopsis sp. from Adenocarpus foliolosus. -Phomosines D-G (I) and (II) as well as acids (III) and (IV) are isolated and tested for their antibacterial, antifungal and herbicidal activity. Only (II) exhibits positive effects. -(DAI, J.; KROHN*, K.; FLOERKE, U.; GEHLE, D.; AUST, H.-J.; DRAEGER, S.; SCHULZ, B.; RHEINHEIMER, J.; Eur. J. Org. Chem. 2005, 23, 5100-5105; Dep. Chem., Univ. Paderborn, D-33098 Paderborn, Germany; Eng.) -Klein 13-212