Communication
ChemComm
4 X. Du, W. Wang, S. Zhang, X. Pu, Q. Zhang, M. Ye, Y. Zhao, B. Wang,
To demonstrate the reliability and practicability of this
photolysis method, we irradiated 1d in the gram-scale (1.3 g,
5.2 mmol) under the optimized conditions and comparable
yield (80% isolated yield) was obtained. We also scaled up the
reaction with S7 (1.2 mmol) and the photolysis efficiently
provided 8 in 86–90% yield, even better than that obtained in
the small scale reaction (see details in the ESI†).
In summary, we have developed a photo-induced C–O bond
formation methodology for the construction of tetrahydrox-
anthones. The photolytic conditions and scope of the photo-
lysis were systematically studied. We found that this mild,
metal-free reaction proceeds under neutral or basic conditions
at room temperature. Various substrates containing electron
rich or deficient aromatic rings and different functional groups
tolerate this photolysis well, giving good to excellent yields. We
also preliminarily used this methodology in the construction of
the basic skeleton of xanthone containing natural products. We
are exploring the total synthesis of kibdelone C and structurally
related polycyclic xanthones using this method.
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Financial support was provided by the NSFC (21102045 and
21272076), the program for professor of special appointment
(Eastern Scholar) at Shanghai institutions of higher learning
and the Program for Changjiang Scholars and Innovative
Research Team in University (PCSIRT).
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