SYNTHETIC COMMUNICATIONS®
253
aqueous layer was extracted with EtOAc (50 mL � 4). The combined organic layer was
dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The
crude product was purified by silica gel column chromatography (Rf ¼ 0.55, 1:1 hexane/
EtOAc) to afford diphenol 7 (0.25 g, 0.95 mmol) in 65% yield as a light pink solid. Data:
IR (KBr) 3362, 2922, 1603, 1510, 1446, 1249, 1170, 1148, 1092, 991, 865, 820, 745,
529 cm−1; 1H NMR (acetone-d6, 400 MHz) δ ¼ 8.35 (s, 2H), 7.14 (d, J ¼ 8.4 Hz, 4H),
6.62 (d, J ¼ 8.4 Hz, 4H), 6.58–6.66 (m, 2H), 6.36 (d, J ¼ 15.2 Hz, 2H), 6.25–6.34 (m, 2H)
ppm; 13C NMR (acetone-d6, 100 MHz) δ ¼ 158.8, 134.4, 133.5, 131.0, 129.3, 128.3, 117.2 ppm;
HRMS (EI): m/z [264.12] calcd for C18H16O2, 264.1150, found 264.1148.
Acknowledgement
This work was supported by 2017 research fund of Myongji University.
ORCID
Sangho Koo
References and notes
[1] Kocienski, P. J. Protecting Groups, 3rd ed.; Georg Thieme Verlag: Stuttgart, 2005, 668.
[2] Wuts, P. G. M.; Green, T. W. Green’s Protective Groups in Organic Synthesis, 4th ed.; Wiley:
New Jersey, 2006.
[3] Scalbert, A.; Jhonson, I. T.; Saltmarsh, M. Polyphenols: antioxidants and beyond. Am. J. Clin.
Nutr. 2005, 81, 215S–217S.
[4] Scalbert, A.; Manach, C.; Morand, C.; Rémésy, C. Dietary Polyphenols and the Prevention of
Diseases. Crit. Rev. Food Sci. Nutr. 2005, 45, 287–306.
[5] Ghosh, A.; Bainbridge, D. T.; Stanley, L. M. Enantioselective Model Synthesis and Progress
toward the Putative Structure of Yuremamine. J. Org. Chem. 2016, 81, 7945–7951.
[6] Ankner, T.; Hilmersson, G. Instantaneous Deprotection of Tosylamides and Esters with SmI2/
Amine/Water. Org. Lett. 2009, 11, 503–506.
[7] Coeffard, V.; Thobie-Gautier, C.; Beaudet, I.; Grognec, E. L.; Quintard, J.-P. Mild Electrochemi-
cal Deprotection of N-Phenylsulfonyl N-Substituted Amines Derived from (R)-Phenylglycinol.
Eur. J. Org. Chem. 2008, 383–391.
[8] Shashidhar, M. S.; Bhatt, M. V. 2-Formylbenzenesulphonyl Chloride as a Reagent for the
Protection of Phenols. J. Chem. Soc., Chem. Commun. 1987, 654–656.
[9] Maeda, H.; Yamamoto, K.; Kohno, I.; Hafsi, L.; Itoh, N.; Nakagawa, S.; Kanagawa, N.;
Suzuki, K.; Uno, T. Design of a Practical Fluorescent Probe for Superoxide Based on
Protection–Deprotection Chemistry of Fluoresceins with Benzenesulfonyl Protecting Groups.
Chem. Eur. J. 2007, 13, 1946–1954.
[10] Ohgiya, T.; Nishiyama, S. A Simple Deprotection of Triflate Esters of Phenol Derivatives.
Tetrahedron Lett. 2004, 45, 6317–6320.
[11] Briot, A.; Baehr, C.; Brouillard, R.; Wagner, A.; Mioskowski, C. Benzylsulfonyl: a Valuable
Protecting and Deactivating Group in Phenol Chemistry. Tetrahedron Lett. 2003, 44, 965–967.
[12] Chang, J. J.; Chan, B.; Ciufolini, M. A. Synthetic Studies Toward Spiroleucettadine. Tetrahedron
Lett. 2006, 47, 3599–3601.
[13] Cons, B. D.; Bunt, A. J.; Bailey, C. D.; Willis, C. L. Total Synthesis of (-)-Blepharocalyxin D and
Analogues. Org. Lett. 2013, 15, 2046–2049.
[14] Tang, J.-J.; Fan, G.-J.; Dai, F.; Ding, D.-J.; Wang, Q.; Lu, D.-L.; Li, R.-R.; Li, X.-Z.; Hu, L.-M.;
Jin, X.-L.; et al. Finding More Active Antioxidants and Cancer Chemoprevention Agents by
Elongating the Conjugated Links of Resveratrol. Free Radical Biol. Med. 2011, 50, 1447–1457.