Synthesis of the fully functionalized core structure of the antibiotic abyssomicin C.
[reaction: see text] The fully functionalized core structure 23 of abyssomicin C (6) containing an oxabicyclooctane ring and a tetronate was prepared via a Diels-Alder approach. After hydroxylation of lactone 10 to the alpha-hydroxylactone 12, lactone opening led to the hydroxy ester 16. A directed epoxidation furnished the desired syn-epoxide 20. Acetylation of the tertiary hydroxyl group, followed by intramolecular Claisen condensation, gave directly the core structure 23.
Rath
Jean-Philippe
JP
Institut für Organische Chemie, Universität Tübingen, Germany.
Kinast
Stephan
S
Maier
Martin E
ME
D000900:Anti-Bacterial Agents; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D019086:Bridged Bicyclo Compounds, Heterocyclic; D007783:Lactones; C509797:abyssomicin C