Annulation approach to doubly linked (A-type) oligocatechins: Syntheses of (+)-procyanidin A2 and (+)-cinnamtannin B1

Angewandte Chemie - International Edition

Volumn 53, Issue 38, 2014, Pages 10129-10133

  Ito, Yuji ^a   Ohmori, Ken ^a   Suzuki, Keisuke ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

annulation; heterocylces; natural products; structure elucidation; total synthesis

Indexed keywords

ORGANIC COMPOUNDS; PHENOLS; STEREOCHEMISTRY; STEREOSELECTIVITY; SULFUR COMPOUNDS;

ANNULATION; HETEROCYLCES; NATURAL PRODUCTS; STRUCTURE ELUCIDATION; TOTAL SYNTHESIS;

FLAVONOIDS;

BIFLAVONOID; CATECHIN; PROANTHOCYANIDIN; PROCYANIDIN A2; PROCYANIDIN B1;

CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BIFLAVONOIDS; CATECHIN; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROANTHOCYANIDINS; STEREOISOMERISM;

EID: 84925442691     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201405600     Document Type: Article

References (39)

1. H. Lou, Y. Yamazaki, T. Sasaki, M. Uchida, H. Tanaka, S. Oka, Phytochemistry 1999, 51, 297-308
2. K. Kamiya, C. Watanabe, H. Endang, M. Umar, T. Satake, Chem. Pharm. Bull. 2001, 49, 551-557.
3. A. B. Bohm, Introduction to Flavonoids, Harwood Academic Publishers, Amsterdam, 1998
4. Plant Polyphenols 2: Chemistry, Biology, Pharmacology, Ecology (Eds.:, G. G. Gross, R. W. Hemingway, T. Yoshida, S. J. Branham,), Kluwer Academic/Plenum Publishers, New York, 1999
5. Flavonoids: Chemistry, Biochemistry and Applications (Eds.:, Ø. M. Andersen, K. R. Markham,), CRC Press/Taylor & Francis, Boca Raton, 2006.
6. S. Morimoto, G. Nonaka, I. Nishioka, Chem. Pharm. Bull. 1985, 33, 4338-4345
7. S. Morimoto, G. Nonaka, I. Nishioka, Chem. Pharm. Bull. 1987, 35, 4717-4729; and a related paper see
8. N.-I. Baek, M.-S. Chung, L. Shamon, L. B. S. Kardono, S. Tsauri, K. Padmawinata, J. M. Pezzuto, D. D. Soejarto, A. D. Kinghorn, J. Nat. Prod. 1993, 56, 1532-1538.
9. R. A. Anderson, C. L. Broadhurst, M. M. Polansky, W. F. Schmidt, A. Khan, V. P. Flanagan, N. W. Schoene, D. J. Graves, J. Agric. Food Chem. 2004, 52, 65-70
10. K. J. Jarvill-Taylor, R. A. Anderson, D. J. Graves, J. Am. Coll. Nutr. 2001, 20, 327-336
11. A. Khan, M. Safdar, M. M. A. Khan, K. N. Khattak, R. A. Anderson, Diabetes Care 2003, 26, 3215-3218.
12. L. Jurd, A. C. Waiss, Jr., Tetrahedron 1965, 21, 1471-1483; related works, see
13. C. Selenski, T. R. R. Pettus, Tetrahedron 2006, 62, 5298-5307
14. G. A. Kraus, Y. Yuan, A. Kempema, Molecules 2009, 14, 807-815.
15. K. Kondo, M. Kurihara, K. Fukuhara, T. Tanaka, T. Suzuki, N. Miyata, M. Toyoda, Tetrahedron Lett. 2000, 41, 485-488.
16. A. P. Kozikowski, W. Tückmantel, C. George, J. Org. Chem. 2000, 65, 5371-5381.
17. Tückmantel and co-workers reported isolation of 2-alkoxy and 2,4-dialkoxy derivatives under similar reaction conditions. See, W. Tückmantel, A. P. Kozikowski, L. J. Romanczyk, Jr., J. Am. Chem. Soc. 1999, 121, 12073-12081.
18. K. Ohmori, N. Ushimaru, K. Suzuki, Proc. Natl. Acad. Sci. USA 2004, 101, 12002-12007
19. K. Ohmori, T. Shono, Y. Hatakoshi, T. Yano, K. Suzuki, Angew. Chem. 2011, 123, 4964-4969
20. Angew. Chem. Int. Ed. 2011, 50, 4862-4867
21. T. Yano, K. Ohmori, H. Takahashi, T. Kusumi, K. Suzuki, Org. Biomol. Chem. 2012, 10, 7685-7688.
22. For the reactivity matching of nucleophile/electrophile which could be used in synthetic reactions. See, H. Mayr, A. R. Ofial, J. Phys. Org. Chem. 2008, 21, 584-595, and references therein.
23. S. Stadlbauer, K. Ohmori, F. Hattori, K. Suzuki, Chem. Commun. 2012, 48, 8425-8427.
24. A. Pleschke, A. Marhold, M. Schneider, A. Kolomeitsev, G.-V. Röschenthaler, J. Fluorine Chem. 2004, 125, 1031-1038
25. C. Heiss, E. Marzi, F. Mongin, M. Schlosser, Eur. J. Org. Chem. 2007, 669-675
26. K. Shen, Y. Fu, J.-N. Li, L. Liu, Q.-X. Guo, Tetrahedron 2007, 63, 1568-1576
27. M. Stratakis, P. G. Wang, A. Streitwieser, J. Org. Chem. 1996, 61, 3145-3150
28. H. Seo, K. Ohmori, K. Suzuki, Chem. Lett. 2011, 40, 744-746.
29. X. Ren, X. Chen, K. Peng, X. Xie, Y. Xia, X. Pan, Tetrahedron: Asymmetry 2002, 13, 1799-1804.
30. CCDC 996429 (21) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
31. N.E. CHEMCAT Co.
32. Funakoshi Co., Ltd. [product No. 0985S (lot No. 14012803), ≥99% purity (HPLC)].
33. A. J. Birch, J. W. Clark-Lewis, A. V. Robertson, J. Chem. Soc. 1957, 3586-3594
34. P. Kiatgrajai, J. D. Wellons, L. Gollob, J. D. White, J. Org. Chem. 1982, 47, 2910-2912
35. P. P. Mehta, W. B. Whalley, J. Chem. Soc. 1963, 5327-5332
36. N. Ishino, E. Yanase, S. Nakatsuka, Biosci. Biotechnol. Biochem. 2010, 74, 875-877.
37. 2O, etc.] failed.
38. A. Saito, N. Nakajima, A. Tanaka, M. Ubukata, Tetrahedron 2002, 58, 7829-7837.
39. 1H NMR)].