Synthesis of arrecatannin A1 (1) was accomplished from dimeric epicatechin electrophile, which was prepared by Zn(OTf)2 mediated self-condensation, and monomeric catechin nucleophile. The condensation was successfully worked using Yb(OTf)3 as a Lewis acid in good yield.
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6.
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7.
FujiiW, TodaK, MatsumotoK, KawaguchiK, KawaharaS-i, HattoriY, FujiiH, MakabeH. (2013) Syntheses of prodelphinidin B1, B2 and B4 and their antitumor activities against human PC-3 prostate cancer cell lines. Tetrahedron Letters, 54, 7188–7192.
8.
SudaM, KatohM, TodaK, MatsumotoK, KawaguchiK, KawaharaS-i, HattoriY, FujiiH, MakabeH. (2013) Syntheses of procyanidin B2 and B3 gallate derivatives using equimolar condensation mediated by Yb(OTf)3 and their antitumor activities. Bioorganic Medicinal Chemistry Letters, 23, 4935–4939.
9.
FujiiW, TodaK, KawaguchiK, KawaharaS.-I, KatohM, HattoriY, FujiiH, MakabeH. (2013) Syntheses of prodelphinidin B3 and C2, and their antitumor activities through cell cycle arrest and caspase-3 activation. Tetrahedron, 69, 3543–3550.
10.
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11.
KatohM, OizumiY, MohriY, HirotaM, MakabeH. (2012) Synthesis of procyanidin B1, B2, and B4 and their anti-inflammatory activity. The effect of 4-alkoxy group of catechin and/or epicatechin electrophiles for condensation. Letters in Organic Chemistry, 9, 233–238.
12.
AlharthyRD, HayesCJ. (2010) Procyanidin B3 synthesis: a study of leaving group and Lewis acid activator effects upon interflavan bond formation. Tetrahedron Letters, 51, 1193–1195.
13.
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14.
MohriY, SagehashiM, YamadaT, HattoriY, MorimuraK, HamauzuY, KamoT, HirotaM, MakabeH. (2009) An efficient synthesis of procyanidins using equimolar condensation of catechin and/or epicatechin catalyzed by ytteribium triflate. Heterocycles, 79, 549–563.
15.
OyamaK, KuwanoM, ItoM, YoshidaK, KondoT. (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-(+)-catachin and (-)-epicatechin as a key building monomer. Tetrahedron Letters, 49, 3176–3180.
16.
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17.
MohriY, SagehashiM, YamadaT, HattoriY, MorimuraK, KamoT, HirotaM, MakabeH. (2007) An efficient synthesis of procyanidins. Rare earth metal Lewis acid catalyzed equimolar condensation of catechin and epicatechin. Tetrahedron Letters, 48, 5891–5894.
18.
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19.
SaitoA, NakajimaN, MatsuuraN, TanakaA, UbukataM. (2004) Synthetic studies of proanthocyanidins: Part 5. Highly stereoselective synthesis and inhibitory activity of Maillard reaction of 3,4-trans catechin and epicatechin dimers, procyanidin B1, B2, B3, B4 and their acetates. Heterocycles, 62, 479–489;
20.
SaitoA, NakajimaN, TanakaA, UbukataM. (2003) Synthetic studies of proanthocyanidins. Part 4. The synthesis of procyanidin B1 and B4: TMSOTf-catalyzed cyclization of catechin and epicatechin condensation. Heterocycles, 61, 287–298.
21.
SaitoA, NakajimaN, MatsuuraN, TanakaA, UbukataM. (2002) Synthetic studies of procyanidins. Part 2: Stereoselective gram-scale synthesis of procyanidin-B3. Tetrahedron, 58, 7829–7837.
22.
Recent syntheses of proanthocyanidin trimers: (a) YanoT, OhmoriK, TakahashiH, KusumiT, SuzukiK. (2012) Unified approach to catechin hetero-oligomers: first total synthesis of trimer-EZ-EG-CA isolated from Ziziphus jujuba. Organic Biomolecular Chemistry, 10, 7685–7688.
23.
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24.
OizumiY, MohriY, HattoriY, MakabeH. (2011) Efficient stereoselective synthesis of catechin trimer derivative using silver Lewis acid catalyzed equimolar condensation. Heterocycles, 83, 739–742.
25.
OhmoriK, UshimaruN, SuzukiK. (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.
26.
SaitoA, DoiY, TanakaA, MatsuuraN, UbukataM, NakajimaN, (2004) Systematic synthesis of four epicatechin series procyanidin trimers and theis inhibitory activity on the Maillard reaction and antioxidant activity. Bioorganic Medicinal Chemistry, 12, 4783–4790.
27.
SaitoA, TanakaA, UbukataM, NakajimaN. (2004) Efficient stereoselective synthesis of proanthocyanidin trimers with TMSOTf-catalyzed intermolecular condensation. Synlett, 1069–1073.
28.
Syntheses of procyanidin oligomers: (a) OhmoriK, ShonoT, HatakoshiY, YanoT, SuzukiK. (2011) Integrated synthetic strategy for higher catechin oligomers. Angewante Chemie International Edition in English, 50, 4862–4867.
29.
SaitoA, MizushinaY, TanakaA, NakajimaN. (2009) Versatile synthesis of epicatechin series procyanidin oligomers, and their antioxidant and DNA polymerse inhibitory activity. Tetrahedron, 65, 7422–7428.
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SudaM, FujiiW, TakanashiK, HattoriY, MakabeH. (2014) Selective synthesis of epicatechin dimers using Zn(OTf)2 mediated self-condensation. Synthesis, 46, 3351–3355.
31.
ShojiT, MutsugaM, NakamuraT, KandaT, AkiyamaH, GodaY. (2003) Isolation and structural elucidation of some procyanidins from apple by low-temperature nuclear magnetic resonance. Journal of Agricultural and Food Chemistry, 51, 3806–3813.
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