Addition of dithiols to bis-ynones: development of a versatile platform for the synthesis of polyketide natural products.
[reaction: see text] The conjugate addition of dithiols to bis-ynones generates a versatile masked 1,3,5-triketone platform. These functional units are useful intermediates for the synthesis of oxygen-containing heterocycles commonly found in polyketide natural products. The tetrahydropyranyl fragments of the marine macrolides Lyngbouilloside and Callipeltoside A have been synthesized with use of this methodology.
Sneddon
Helen F
HF
University Chemical Laboratory, Lensfield Road, Cambridge, UK CB2 1EW.
Gaunt
Matthew J
MJ
Ley
Steven V
SV
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D000900:Anti-Bacterial Agents; D001688:Biological Products; D006027:Glycosides; D007659:Ketones; D018942:Macrolides; D013438:Sulfhydryl Compounds; C410329:callipeltoside A; C464989:lyngbouilloside