Synthesis, Table of Contents Synthesis 2015; 47(04): 485-488DOI: 10.1055/s-0034-1379582 paper © Georg Thieme Verlag Stuttgart · New York Synthesis of Yangjinhualine A Prashant S. Deore Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India Email: np.argade@ncl.res.in , Ramesh U. Batwal Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India Email: np.argade@ncl.res.in , Narshinha P. Argade* Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India Email: np.argade@ncl.res.in › Author Affiliations Recommend Article Abstract Buy Article All articles of this category Abstract Selective reduction of 3-(4-hydroxyphenyl)-2-methylmaleic anhydride provides access the corresponding γ-hydroxybutenolide natural product yangjinhualine A. Key words Key wordsanhydrides - regioselectivity - reduction - lactones - natural products Full Text References References 1a Deore PS, Argade NP. Synthesis 2014; 46: 281 1b Clark B, Capon RJ, Lacey E, Tennant S, Gill JH, Bulheller B, Bringmann G. J. Nat. Prod. 2005; 68: 1226 1c Fujimoto H, Satoh Y, Yamaguchi K, Yamazaki M. Chem. Pharm. Bull. 1998; 46: 1506 1d Rao YS. Chem. Rev. 1976; 76: 625 2a Margarucci L, Tosco A, De Simone R, Riccio R, Monti MC, Casapullo A. ChemBioChem 2012; 13: 982 2b Michel K, Büther K, Law MP, Wagner S, Schober O, Hermann S, Schäfers M, Riemann B, Höltke C, Kopka K. J. Med. Chem. 2011; 54: 939 2c Aquino M, Guerrero MD, Bruno I, Terencio MC, Paya M, Riccio R. Bioorg. Med. Chem. 2008; 16: 9056 2d Wang GJ, Chen SM, Chen WC, Chang YM, Lee TH. J. Ethnopharmacol. 2007; 112: 221 2e Paulitz T, Nowak-Thompson B, Gamard P, Tsang E, Loper J. J. Chem. Ecol. 2000; 26: 1515 3a Kuang H, Yang B, Xia Y, Feng W. Arch. Pharmacal. Res. 2008; 31: 1094 3b Fujimoto H, Asai T, Kim Y.-P, Ishibashi M. Chem. Pharm. Bull. 2006; 54: 550 3c Wu M.-D, Cheng M.-J, Wang B.-C, Yech Y.-J, Lai J.-T, Kuo Y.-H, Yuan G.-F, Chen I.-S. J. Nat. Prod. 2008; 71: 1258 3d Xu Y.-J, Tang C.-P, Tan M.-J, Ke C.-Q, Wu T, Ye Y. Chemistry & Biodiversity 2010; 7: 151 4a Parker AN, Lock MJ, Hutchison JM. Tetrahedron Lett. 2013; 54: 5322 4b Lamberth C, Godineau E, Smejkal T, Trah S. Tetrahedron Lett. 2012; 53: 4117 4c Yamano Y, Fujita Y, Mizuguchi Y, Nakagawa K, Okano T, Ito M, Wada A. Chem. Pharm. Bull. 2007; 55: 1365 4d De Rosa S, Puliti R, Crispino A, De Giulio A, De Sena C, Iodice C, Mattia CA. Tetrahedron 1995; 51: 10731 5a Boukouvalas J, Albert V, Loach RP, Lafleur-Lambert R. Tetrahedron 2012; 68: 9592 5b Boukouvalas J, McCann LC. Tetrahedron Lett. 2011; 52: 1202 ; and references cited therein 6a Margaros I, Vassilikogiannakis G. J. Org. Chem. 2008; 73: 2021 6b Patil SN, Stephens BE, Liu F. Tetrahedron 2008; 64: 10831 6c Clive DL, Ou L. J. Org. Chem. 2005; 70: 3318 7 Ma S, Wu B, Shi Z. J. Org. Chem. 2004; 69: 1429 8 Chinese Herbology. Wikipedia. Web site. http://en.wikipedia.org/wiki/Chinese_herbology#50_fundamental_herbs (accessed Nov 4, 2014). 9a Yang B.-Y, Xia Y.-G, Wang Q.-H, Dou D.-Q, Kuang H.-X. Fitoterapia 2010; 81: 1003 9b Kuang H, Yang B, Tang L, Xia Y, Dou D. Helv. Chim. Acta 2009; 92: 1315 10 Wagner, R. A.; Tropane Alkaloid Poisoning. Medscape. Web site. http://emedicine.medscape.com/article/816657-overview (accessed Nov 4, 2014). 11 Krenzelok EP. Clin. Toxicol. 2010; 48: 104 12 Zhou H, Yang Y, Peng T, Li W, Zhao L, Xu L, Ding Z. Nat. Prod. Res. 2014; 28: 265 13a Deore PS, Argade NP. J. Org. Chem. 2014; 79: 2538 13b Deore PS, Argade NP. Org. Lett. 2013; 15: 5826 13c Patel RM, Puranik VG, Argade NP. Org. Biomol. Chem. 2011; 9: 6312 14 Fields EK, Behrend SJ, Meyerson S, Winzenburg ML, Ortega BR, Hall HK. Jr. J. Org. Chem. 1990; 55: 5165 15 Deore PS, Argade NP. J. Org. Chem. 2012; 77: 739 ; and references cited therein 16 Boukouvalas J, Albert V. Heterocycles 2014; 88: 939 17 Naganawa A, Ichikawa Y, Isobe M. Tetrahedron 1994; 50: 8969 Supplementary Material Supplementary Material Supporting Information
