Total Syntheses of Allelopathic 4-Oxyprotoilludanes, Melleolides, and Echinocidins

Autor:	Ken-ichi Yamada, Hiroshi Takikawa, Kazuma Shimoda, Yousuke Yamaoka, Dongeun Yoo, Kiyosei Takasu
Rok vydání:	2019
Předmět:	Silylation 010405 organic chemistry Stereochemistry Chemistry Organic Chemistry Hydroxy group Acetal Ketene 010402 general chemistry 01 natural sciences Cycloaddition 0104 chemical sciences chemistry.chemical_compound Intramolecular force Allelopathy
Zdroj:	The Journal of Organic Chemistry. 84:11014-11024
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.9b01589
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::8c9a142bb74d7e2c705428215d52281e https://doi.org/10.1021/acs.joc.9b01589 Zobrazit plný text záznamu