The first total synthesis of the dimeric berberine alkaloid ilicifoline (ilicifoline B) is reported. Its carbon skeleton is constructed from ferulic acid, veratrole, and methanol. The synthesis reported herein employs starting materials solely derived from wood. The natural product is thus constructed entirely from renewable resources. The same strategy is applied to a formal total synthesis of morphinan alkaloids. The use of wood-derived building blocks (xylochemicals) instead of the conventional petrochemicals represents a sustainable alternative to classical synthetic approaches.

Die erste Totalsynthese des dimeren Berberin-Alkaloids Ilicifolin (Ilicifolin B) wird beschrieben. Sein Kohlenstoffgerüst wird dabei aus Ferulasäure, Veratrol und Methanol aufgebaut – Bausteine, die aus Holz als nachwachsendem Rohstoff gewonnen werden können. Die gleiche Strategie wurde für eine formale Totalsynthese von Morphinan-Alkaloiden genutzt. Die Verwendung von Ausgangsmaterialien auf Holzbasis (Xylochemikalien) anstelle von Petrochemikalien stellt eine nachhaltige Alternative zu klassischen Synthesestrategien dar.

Novel bis(imidazole-2-thion-4-yl)- phosphanes (2a–d) were synthesized via lithiation of the precursor imidazole-2-thiones followed by the phosphanylation reaction. Oxidation of bis(imidazole-2-thion-4-yl)phosphane 2b–d with elemental sulfur and selenium led selectively and in good yields to the P-thio (3b–d) and P-seleno (4c) derivatives of bis(imidazole-2-thion-4-yl)phosphanes, respectively. The treatment of 2a,c with phosphorus trichloride gives the corresponding P-chloro derivatives 5a,c. These compounds were unambiguously characterized by elemental analyses, spectroscopic and spectrometric methods, in addition by single-crystal X-ray structure analysis in the case of 2d. © 2012 Wiley Periodicals, Inc. Heteroatom Chem 00:1–7, 2012; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.21043