Synthesis, Inhaltsverzeichnis REVIEW © Georg Thieme Verlag Stuttgart ˙ New York Synthesis of Oximinotyrosine-Derived Marine Natural Products Fabia Hentschel, Thomas Lindel*Institute of Organic Chemistry, TU Braunschweig, Hagenring 30, 38106 Braunschweig, Germany Fax: +49(531)3917744; e-Mail: th.lindel@tu-bs.de; Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract This review article gives a detailed account on the synthesis of oximinotyrosine-derived marine natural products from sponges of the order Verongida. Oxidation of the amino group of the underlying bromotyrosine building block to the oxime gives rise to unique chemistry. One of the key features of the peptide-like bromotyrosine compounds is their ability to undergo cyclization to spiroisoxazolines and to form diaryl ether linkages. 1 Introduction 2 Open-Chain α-Oximinoamides 2.1 Psammaplin A 2.2 Spermatinamine, Purealidin, Verongamine 2.3 Psammaplysenes 3 Macrocyclic α-Oximinoamides 3.1 Bastadins 3.2 Bastadin Models 4 Spirocyclized α-Oximinoamides 4.1 Aerothionin 4.2 Calafianin 4.3 Purealin A 4.4 Psammaplysin 5 Aeroplysinin-1 6 Summary and Challenges Key words marine natural products - bromotyrosine - spirocyclization - diaryl ether - oxime Volltext Referenzen References 1 Peng J. Li J. Hamann MT. The Alkaloids: Chemistry and Biology 2005, 61: 59-262 2 Rahboek L. Christophersen C. The Alkaloids: Chemistry and Biology 2001, 57: 185-233 3 Harayama Y. Kita Y. Curr. Org. Chem. 2005, 9: 1567 4 Fan H. Peng J. Hamann MT. Hu J.-F. Chem. Rev. 2008, 108: 264 5a Thompson JE. Barrow KD. Faulkner DJ. Acta Zoolog. 1983, 64: 199 5b Simmons TL. Coates RC. Clark BR. 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