Total Synthesis of Naturally Occurring Furan Compounds 5-{[(4-Hydroxybenzyl)oxy]methyl}-2-furaldehyde and Pichiafuran C

Abstract

The synthesis of the natural furan derivatives 5-{[(4-hydroxybenzyl)oxy]methyl}-2-furaldehyde and pichiafuran C is described. Diverse alternative synthetic approaches were developed for the preparation of these natural products. They were prepared through an etherification reaction of the key furan precursor 5-(hydroxymethyl)-2-furaldehyde (HMF), which can be readily obtained from d-fructose, d-glucose, or sucrose, with the corresponding alcohols. 5-{[(4-Hydroxybenzyl)oxy]methyl}-2-furaldehyde was not only obtained in a two-step methodology but also by a biomimetic single-step synthesis. Similarly, pichiafuran C was prepared by three different syntheses, each one by a two-step procedure, also including a biomimetic approach.

Key words

5-{[(4-hydroxybenzyl)oxy]methyl}-2-furaldehyde - pichiafuran C - 5-(hydroxymethyl)-2-furaldehyde - Gastrodia elata Blume - Pichia membranifaciens

References

• 1 Lee Y.-K. Woo M.-H. Kim C.-H. Kim Y. Lee S.-H. Jeong B.-S. Chang H.-W. Son J.-K. Planta Med.  2007,  73:  1287 
• 2a Hus HY. Chen YP. Hsu SJ. Hsu CS. Chen CC. Chang HC. Oriental Materia Medica: A Concise Guide   Oriental Health Art Institute; California: 1986.  p.662 
• 2b Tang W. Eisenbrand G. Chinese Drugs of Plant Origin, Chemistry, Pharmacology, and Use in Traditional and Modern Medicine   Springer Verlag; Berlin: 1992.  p.545-548  
• 2c Hayashi J. Sekine T. Deguchi S. Lin Q. Horie S. Tsuchiya S. Yano S. Watanabe K. Ikegami F. Phytochemistry  2002,  59:  513 
• 3a Hsieh M.-T. Wu C.-R. Chen C.-F. J. Ethnopharmacol.  1997,  56:  45 
• 3b Wu C.-R. Hsieh MT. Huang S.-C. Peng W.-H. Chang Y.-S. Chen C.-F. Planta Med.  1996,  62:  317 
• 4 Elbandy M. Shinde PB. Dang HT. Hong J. Bae KS. Jung JH. J. Nat. Prod.  2008,  71:  869 
• 5 Jadulco R. Proksch P. Wray V. . Berg A. Gräfe U. J. Nat. Prod.  2001,  64:  527 
• 6 Shen Y.-C. Prakash CVS. Kuo Y.-H. J. Nat. Prod.  2001,  64:  324 
• 7a Quiroz-Florentino H. Aguilar R. Santoyo BM. Díaz F. Tamariz J. Synthesis  2008,  1023 
• 7b Quiroz-Florentino H. García A. Burgueño-Tapia E. Tamariz J. Nat. Prod. Res.  2009,  23:  1355 
• 8a Kamm B. Angew. Chem. Int. Ed.  2007,  46:  5056 
• 8b Metzger JO. Angew. Chem. Int. Ed.  2006,  45:  696 
• 8c Kröger M. Prüße U. Vorlop K.-D. Top. Catal.  2000,  13:  237 
• 8d Marshall A.-L. Alaimo PJ. Chem. Eur. J.  2010,  16:  4970 
• 9a Mascal M. Nikitin EB. Angew. Chem. Int. Ed.  2008,  47:  7924 
• 9b Li C. Zhang Z. Zhao ZK. Tetrahedron Lett.  2009,  50:  5403 
• 10a Binder JB. Raines RT. J. Am. Chem. Soc.  2009,  131:  1979 
• 10b Yoon H.-J. Choi J.-W. Cho JK. Lee Y.-S. Appl. Chem.  2010,  14:  41 
• 11a Román-Leshkov Y. Barrett CJ. Liu ZY. Dumesic JA. Nature  2007,  447:  982 
• 11b Zhao H. Holladay JE. Brown H. Zhang ZC. Science  2007,  316:  1597 
• 11c Yong G. Zhang Y. Ying JY. Angew. Chem. Int. Ed.  2008,  47:  9345 
• 12 Halliday GA. Young RJ. Grushin VV. Org. Lett.  2003,  5:  2003 
• 13 Perez-Locas C. Yaylayan VA. J. Agric. Food Chem.  2008,  56:  6717 
• 14 Lilga MA. Hallen RT. Gray M. Top. Catal.  2010,  53:  1264 
• 15 Greene TW. Wuts PGM. Protective Groups in Organic Synthesis   Wiley; New York: 1999.  p.250-251  
• 16 Zeynizadeh B. Behyar T. J. Braz. Chem. Soc.  2005,  16:  1200 
• 17 Pyo MK. Jin JL. Koo YK. Yun-Choi HS. Arch. Pharm. Res.  2004,  27:  381 
• 18 Kawada A. Yasuda K. Abe H. Harayama T. Chem. Pharm. Bull.  2002,  50:  380 
• 19a Hamada K. Yoshihara H. Suzukamo G. Chem. Lett.  1982,  617 
• 19b Chakraborty TK. Tapadar S. Kumar SK. Tetrahedron Lett.  2002,  43:  1317 
• 19c Hamada K. Yoshihara H. Suzukamo G. J. Oleo Sci.  2001,  50:  533 
• 21 Brun KA. Linden A. Heimgartner H. Helv. Chim. Acta  2002,  85:  3422 
• 22 Faler CA. Joullié MM. Org. Lett.  2007,  9:  1987 
• 23 Kopka K. Faust A. Keul P. Wagner S. Breyholz H.-J. Höltke C. Schober O. Schäfers M. Levkau B. J. Med. Chem.  2006,  49:  6704 
• 24a Collado D. Perez-Inestrosa E. Suau R. Lopez-Navarrete JT. Tetrahedron  2006,  62:  2927 ; and references cited therein
• 24b Dale WJ. Hennis HE. J. Am. Chem. Soc.  1956,  78:  2543 
• 24c Levacher V. Moberg C. React. Polym.  1995,  24:  183 
• 25 Rahman A. Jonnalagadda SB. J. Mol. Catal. A: Chem.  2009,  299:  98 
• 26 Papanov G. Malakov P. Tomova K. Nauchni
  Tr.-Plovdivski Univ. Paisii Khilendarski  1990,  28:  65 ; Chem. Abstr. 1995, 122, 265153

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