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Synthesis of the Pyrrole-Imidazole Alkaloid Sventrin from the Marine Sponge Agelas sventres
| Content Provider | Semantic Scholar |
|---|---|
| Author | Breckle, Gregor Polborn, Kurt Lindel, Thomas |
| Copyright Year | 2003 |
| Abstract | Gregor Breckle, Kurt Polborn, and Thomas Lindel Ludwig-Maximilians-Universität München, Department of Chemistry, Butenandtstr. 5Ð13, D-81377 Munich, Germany Reprint requests to Prof. Dr. Th. Lindel. Fax int: +(0)89/2180-7-7734. E-mail: thomas.lindel@cup.uni-muenchen.de Z. Naturforsch. 58b, 451Ð456 2003; received February 17, 2003 The marine pyrrole-imidazole alkaloid sventrin (1) and the hitherto unknown dehydrooroidin (3) have been synthesized stereoselectively via alkyne intermediates. The pathways start from a 2-azido-4-alkynylimidazole which can be chemoand stereoselectively reduced to the corresponding amino alkene using NaAlH2(OCH2CH2OMe)2 (Red-Al) or, alternatively, to the amino alkyne. Selective removal of simultaneously present Boc or trityl protecting groups was possible employing either p-TsOH or acetic resp. formic acid. |
| File Format | PDF HTM / HTML |
| Alternate Webpage(s) | http://www.znaturforsch.com/ab/v58b/58b0451.pdf |
| Alternate Webpage(s) | http://www.znaturforsch.com/ab/v58b/s58b0451.pdf |
| Language | English |
| Access Restriction | Open |
| Subject Keyword | Agelas Alkaloids Alkenes Alkynes Amino Acid Metabolism, Inborn Errors Dacarbazine Email Fax Imidazoles Pyrroles Reprint formic acid negative regulation of ergot alkaloid biosynthetic process sventrin |
| Content Type | Text |
| Resource Type | Article |
