期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 85, 期 2, 页码 1054-1061出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02983
关键词
-
资金
- University of the Witwatersrand
- South African National Research Foundation (NRF) [85964, 93447, 105839]
Modular gram-scale syntheses of the trimethyl ethers of lamellarins G (6) and D (7) were achieved from readily accessible precursors in the highest overall yields reported to date (6, six steps, 82%; 7, seven steps, 86%). A novel demethylative lactonization between an aryl methyl ether and a neighboring carboxylic acid was developed for creating the chromenone unit of the targets to avoid the need for additional protection and deprotection steps. The central pyrrole core was constructed in a late-stage [4 + 1] condensation between ethyl bromoacetate and an enaminone possessing the remaining components of the lamellarin skeleton. Exhaustive demethylation of both permethyl ethers 6 and 7 gave the polyphenolic natural lamellarins A4 (3) and H (5), respectively.
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