Concise strategy to the core structure of the macrolide queenslandon.
The fully functionalized core structure of the macrolactone queenslandon was prepared using a novel strategy consisting of a glycolate aldol reaction and hydroboration of the derived enol ether 17 followed by Suzuki cross-coupling with an iodostyrene. After conversion of the cross-coupling product to the seco acid 22, Mitsunobu macrolactonization and protecting group manipulations led to the queenslandon model 5. [structure: see text]
Khartulyari
Anton S
AS
Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany.
Kapur
Manmohan
M
Maier
Martin E
ME
D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D000935:Antifungal Agents / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D018942:Macrolides / Q000138:chemical synthesis*; D009285:Naphthoquinones / Q000138:chemical synthesis*; D010084:Oxidation-Reduction
D000447:Aldehydes; D000475:Alkenes; D000935:Antifungal Agents; D018942:Macrolides; D009285:Naphthoquinones; C462599:queenslandon