Total synthesis of (+/-) tanikolide.
The natural polyketide (+/-)-tanikolide (1) was prepared in eight steps starting from hex-5-enol. Key steps in this synthesis are a Sharpless dihydroxylation and a Grignard reaction between an alkyl halogenide and a ketone. The lactonization occurred spontaneously during the oxidation of the primary alcohol function to the carboxy group.
Krauss
J
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Department Pharmazie-Zentrum für Pharmaforschung, Ludwig-Maximilians-Universität München, Munich, Germany.
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001234:Aspergillus niger / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D002384:Catalysis; D004926:Escherichia coli / Q000187:drug effects; D006900:Hydroxylation; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D013058:Mass Spectrometry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010084:Oxidation-Reduction; D011549:Pseudomonas / Q000187:drug effects; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D013210:Staphylococcus / Q000187:drug effects; D013752:Tetracycline / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D007783:Lactones; C400156:tanikolide; D013752:Tetracycline