Journal of Organic Chemistry p. 4319 - 4328 (2013)
Update date:2022-09-26
Topics:
Michihata, Naoki
Kaneko, Yuki
Kasai, Yusuke
Tanigawa, Kotaro
Hirokane, Tsukasa
Higasa, Sho
Yamada, Hidetoshi
This paper describes a total synthesis of (-)-strictinin, an ellagitannin that is 1-O-galloyl-4,6-O-(S)-hexahydroxydiphenoyl (HHDP)-β-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 intramolecular 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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