Synthesis of cladobotryal, CJ16,169, and CJ16,170.
Condensation of hydroxypyridone 7 with ethyl pyruvate and p-chlorothiophenol, reduction, and cyclization afforded 77% of lactone 6. Protection of the pyridone, acylation of the enolate with tigloyl chloride, and deprotection provided keto lactone 22. Reduction and dehydrative cyclization completed short and efficient syntheses of 2 and 3.
Department of Chemistry MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA. snider@brandeis.edu
Barry B
BB
Snider
Qinglin
Q
Che
D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011728:Pyridones / Q000138:chemical synthesis* / Q000737:chemistry
C112140:2-(2-buten-2-yl)-3,7-dihydro-3-formyl-3-methyl-5-phenylfuro(2,3-b)pyridin-4(2H)-one; C503258:CJ16,169; C503257:CJ16,170; D005663:Furans; D007783:Lactones; D011728:Pyridones