Recent Advances in Polyphenol Research. Группа авторов

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and its bis‐2,4‐epi isomer 74 in 29% overall yield from 73α, respectively.

      1 Alejo‐Armijo, A., Parola, A. J., Pina, F., Altarejos, J., and Salido, S. (2018). Thermodynamic stability of flavylium salts as a valuable tool to design the synthesis of A‐type proanthocyanidin analogues. The Journal of Organic Chemistry 83: 12297–12304.

      2 Balde, A., de Bruyne, T., Pieters, L., et al. (1995). Tetrameric proanthocyanidins containing a double interflavanoid (A‐type) linkage from Pavetta owariensis. Phytochemistry 40: 933–938.

      3 Betkekar, V.V., Harachi, M., Suzuki, K., and Ohmori, K. (2019). Syntheses of doubly linked proanthocyanidins using free flavan units as nucleophiles: insight into the origin of the high regioselectivity of annulation. Organic & Biomolecular Chemistry 17: 9129–9134.

      4 Ito, Y., Ohmori, K. and Suzuki, K. (2014). Annulation approach to doubly linked (A‐type) oligocatechins: syntheses of (+)‐procyanidin A2 and (+)‐cinnamtannin B1. Angewandte Chemie International Edition 53: 10129–10133.

      5 Jacques, D., Haslam, E., Bedford, G.R., and Greatbanks, D. (1973). Structure of the dimeric proanthocyanidin A2 and its derivatives. Journal of the Chemical Society, Chemical Communications 518–520.

      6 Jacques, D., Haslam, E., Bedford, G.R., and Greatbanks, D. (1974). Plant proanthocyanidins. Part II. Proanthocyanidin A2 and its derivatives. Journal of the Chemical Society, Perkin Transactions 1: 2663–2671.

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      8 Kondo, K., Kurihara, M., Fukuhara, K., et al. (2000). Conversion of procyanidin B‐type (catechin dimer) to A‐type: evidence for abstraction of C‐2 hydrogen in catechin during radical oxidation. Tetrahedron Letters 41: 485–488.

      9 Kozikowski, A.P. and Tückmantel, W. (2009). Methods for synthesizing the cocoa‐derived oligomeric epi‐catechins – observations on the anticancer activity of the cocoa polyphenols. In: Recent Advances in Polyphenol Research (eds. Daayf, F. and Lattanzio, V., 88–112. Wiley.

      10 Kraus, G.A., and Geraskin, I.M. (2017). Rapid assembly of the procyanidin A skeleton. Tetrahedron Letters 58: 4609–4611.

      11 Kraus, G.A., Yuan, Y., and Kempema, A. (2009). A convenient synthesis of type A procyanidins. Molecules 14: 807–815.

      12 Makabe, H. (2013). Recent syntheses of proanthocyanidins. Heterocycles 87: 2225–2248.

      13 Mayer, W. Goll, L., Arndt, E.M.V., and Mannschreek, A. (1966). Procyanidino‐(–)‐epicatechin, ein zweiarmig verknüpftes, kondensiertes proanthocyanidin aus Aesculus hippocastanum. Tetrahedron Letters 7: 429–435.

      14  Morimoto, S., Nonaka, G., and Nishioka, I. (1985). Tannins and related compounds. XXXV. Proanthocyanidins with a doubly linked unit from the root bark of Cinnamomum sieboldii MEISNER. Chemical and Pharmaceutical Bulletin 33: 4338–4345.

      15 Morimoto, S., Nonaka, G., and Nishioka, I. (1987). Tannins and related compounds. LIX. Aesculitannins, novel proanthocyanidins with doubly‐bonded structures from Aesculus hippocastanum L. Chemical and Pharmaceutical Bulletin 35: 4717–4729.

      16 Nam, J.W., Phansakkar, R.S., Lankin, D.C., et al. (2017). Absolute configuration of native oligomeric proanthocyanidins with dentin biomodification potency. The Journal of Organic Chemistry 82: 1316–1329.

      17 Noguchi, Y., Takeda, R., Suzuki, K., and Ohmori, K. (2018). Total synthesis of selligueain A, a sweet flavan trimer. Organic Letters 20: 2857–2861.

      18 Nonaka, G.‐I., Morimoto, S., Kinjo, J.‐E., et al. (1987). Tannins and related compounds. L structures of proanthocyanidin A‐1 and related compounds. Chemical and Pharmaceutical Bulletin 35: 149–155.

      19 Nonaka, G.‐I., Morimoto, S. and Nishioka, I. (1983). Tannins and related compounds. Part 13. Isolation and structures of trimeric, tetrameric, and pentameric proanthocyanidins from cinnamon. Journal of the Chemical Society, Perkin Transactions 1: 2139–2145.

      20 Ohmori, K., Shono, T., Hatakoshi, Y., et al. (2011). Integrated synthetic strategy for higher catechin oligomers. Angewandte Chemie International Edition 50: 4862–4867.

      21 Ohmori, K., Ushimaru, N. and Suzuki, K. (2004). Oligomeric catechins: an enabling synthetic strategy by orthogonal activation and C(8) protection. Proceedings of the National Academy of Sciences of the United States of America 101: 12002–12007.

      22 Oyama, K.‐I., Kuwano, M., Ito, M., et al. (2008). Synthesis of procyanidins by stepwise‐ and self‐condensation using 3,4‐cis‐4‐acetoxy‐3‐O‐acetyl‐4‐dehydro‐5,7,3',4'‐tetra‐O‐benzyl‐(+)‐catechin and (–)‐epicatechin as a key building monomer. Tetrahedron Letters 49: 3176–3180.

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      24 Saito, A, Mizushina, Y., Tanaka, A. and Nakajima, N. (2009). Versatile synthesis of epicatechin series procyanidin oligomers, and their antioxidant and DNA polymerase inhibitory activity. Tetrahedron 65: 7422–7428.

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      26 Sharma, P.K., Romanczyk, L.J., Jr., Kondaveti, L., et al. (2015). Total synthesis of proanthocyanidin A1, A2, and their stereoisomers. Organic Letters 17: 2306–2309.

      27 Stadlbauer, S., Ohmori, K., Hattori, F., and Suzuki, K. (2012). A new synthetic strategy for catechin‐class polyphenols: concise synthesis of (–)‐epicatechin and its 3‐O‐gallate. Chemical Communications 48: 8425–8427.

      28 Van Rooyen, P.H., and Redelinghuys, H.J.P. (1983). Crystal structure and molecular conformation of proanthocyanidin‐A2, a bitter substance in litchis (Litchi chinensis Sonn.). South African Journal of Chemistry 36: 49–53.

      29 Weinges, K., Kaltenhäuser, W., Marx, H.‐D., et al. (1968). Zur kenntnis der proanthocyanidine, X. Procyanidine aus früchten. Justus Liebigs Annalen der Chemie 711: 184–204.

      30 Weinges, K. and Theobald, H. (1971). Synthese des 6‐phenyl‐12H‐6.12‐methano‐dibenzo[d.g][1.3]‐dioxocins, einer modellsubstanz für die C30H24O12‐procyanidine. Justus Liebigs Annalen der Chemie 743: 203–206.

      31  Xia, L., Cai, H., and Lee, Y.R. (2014). Catalyst‐controlled regio‐ and stereoselective synthesis of diverse 12H‐6,12‐methanodibenzo[d,g][1.3]dioxocines. Organic and Biomolecular Chemistry 12: 4386–4396.

      32 Yang, Z., He, Y. and Toste, F.D. (2016). Biomimetic approach to the catalytic enantioselective synthesis of flavonoids. Journal of the American Chemical Society 138: 9775–9778.

      33 Yano, T., Ohmori, K., Takahashi, H., et al. (2012). Unified approach to catechin hetero‐oligomers: first total synthesis of trimer EZ‐EG‐CA isolated from Ziziphus jujuba. Organic and Biomolecular Chemistry 10: 7685–7688.


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