期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 17, 页码 11014-11024出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01589
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资金
- JSPS KAKENHI [JP16H05073, JP19H03350]
- MEXT KAKENHI [JP16H01147, JP18H04406]
Stereocontrolled total syntheses of allelopathic 4-oxyprotoilludane sesquiterpenes, melleolide, melleolide F, and echinocidins B and D were achieved. The curved 5/6/4 tricyclic system with an angular hydroxy group was built via three key transformations: (1) Me3Al-catalyzed [2 + 2] cycloaddition of a ketene silyl acetal with a propiolate, (2) reductive ring-opening of a cyclic hemiketal, and (3) the intramolecular Morita-Baylis-Hillman reaction. This synthetic route represents a new and reliable strategy to obtain protoilludanes with several oxy-functional groups.
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