600700-71-8Relevant articles and documents
Total Syntheses of Allelopathic 4-Oxyprotoilludanes, Melleolides, and Echinocidins
Shimoda, Kazuma,Yamaoka, Yousuke,Yoo, Dongeun,Yamada, Ken-ichi,Takikawa, Hiroshi,Takasu, Kiyosei
, p. 11014 - 11024 (2019)
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.
An enantiodivergent trend in microbial Baeyer-Villiger oxidations of functionalized pentalenones by recombinant whole cells expressing monooxygenases from Acinetobacter and Pseudomonas
Mihovilovic, Marko D.,Mueller, Bernhard,Schulze, Alexander,Stanetty, Peter,Kayser, Margaret M.
, p. 2243 - 2249 (2007/10/03)
We have investigated the microbial Baeyer-Villiger oxidations of pentalenones by recombinant whole cells expressing cyclohexanone monooxygenase from Acinetobacter and cyclopentanone monooxygenase from Pseudomonas. The two enzymes display a distinguishable