期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 78, 期 9, 页码 4319-4328出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo4003135
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资金
- JSPS KAKENHI [22550047]
- SUBOR grant
- Grants-in-Aid for Scientific Research [22550047] Funding Source: KAKEN
This paper describes a total synthesis of (-)-strictinin, an ellagitannin that is 1-O-galloyl-4,6-O-(S)-hexahydroxydiphenoyl (HHDP)-beta-D-glucose. In the study, total efficiency of the synthesis was improved to produce a 78% overall yield in 13 steps from D-glucose. In the synthesis, formation of the 4,6-(S)-HHDP bridge including the 11-membered bislactone ring was a key step, in which intramoleular aryl-aryl coupling was adopted. The coupling was oxidatively induced by CuCl2-n-BuNH2 with perfect control of the axial chirality, and the reaction conditions of this coupling were optimized thoroughly to achieve the quantitative formation of the bridge.
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