Synthesis and antifungal activity of 7-methyl-7-hydroxy-2,3-benzo[c]octa-1,6-olide.
The racemic 7-methyl-7-hydroxy-2,3-benzo[c]octa-1,6-olide, the analog of natural product (6R)-3,7-dimethyl-7-hydroxy-2-octen-1,6-olide, was totally synthesized using easily available (E)-2-(2-carboxyvinyl)benzoic acid as a raw material in nine-step reactions including three key steps of Wittig reaction, epoxidation, and cyclization, with an overall yield of 10.3%. The bioassay results showed that ( ± )-2 exhibited stronger antifungal activity than the natural product ( ± )-1 and (R)-1 against Alternaria solani with an EC₅₀ value of 27.36 μg/ml.
a Department of Applied Chemistry , College of Sciences, China Agricultural University , Beijing , 1000193 , China.
Jin
J
Zhao
Hong-Bo
HB
Dong
Ming-Yan
MY
Yang
Juan
J
Du
Jia-Zheng
JZ
Jiang
Ming-An
MA
Wang
D000528:Alternaria / Q000187:drug effects*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D003500:Cyclization; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
C587302:7-methyl-7-hydroxy-2,3-benzo(c)octa-1,6-olide; D000935:Antifungal Agents; D001688:Biological Products; D013729:Terpenes