Synthesis 2015; 47(22): 3513-3521
DOI: 10.1055/s-0034-1378812
paper
© Georg Thieme Verlag Stuttgart · New York

Stereocontrolled Total Syntheses of Optically Active Furofuran Lignans

Makoto Inai
School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka, 422-8526, Japan   Email: [email protected]   Email: [email protected]
,
Ryo Ishikawa
School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka, 422-8526, Japan   Email: [email protected]   Email: [email protected]
,
Naoto Yoshida
School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka, 422-8526, Japan   Email: [email protected]   Email: [email protected]
,
Nana Shirakawa
School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka, 422-8526, Japan   Email: [email protected]   Email: [email protected]
,
Yusuke Akao
School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka, 422-8526, Japan   Email: [email protected]   Email: [email protected]
,
Yusuke Kawabe
School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka, 422-8526, Japan   Email: [email protected]   Email: [email protected]
,
Tomohiro Asakawa
School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka, 422-8526, Japan   Email: [email protected]   Email: [email protected]
,
Masahiro Egi
School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka, 422-8526, Japan   Email: [email protected]   Email: [email protected]
,
Yoshitaka Hamashima*
School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka, 422-8526, Japan   Email: [email protected]   Email: [email protected]
,
Toshiyuki Kan*
School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka, 422-8526, Japan   Email: [email protected]   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 25 May 2015

Accepted after revision: 14 June 2015

Publication Date:
12 August 2015 (online)


Abstract

Plant products (+)-sesamin, (+)-sesaminol, (+)-methylpiperitol, (+)-aschantin, and (+)-5'-hydroxymethylpiperitol were synthesized in a highly stereocontrolled manner through l-proline-catalyzed bifunctional-urea-accelerated cross-aldol reaction, followed by biomimetic construction of the furofuran lignan skeleton through a quinomethide intermediate.

Supporting Information

 
  • References


    • For general reviews on lignans, see:
    • 1a Zhang J, Chen J, Liang Z, Zhao C. Chem. Biodivers. 2014; 11: 1
    • 1b Ward RS. Nat. Prod. Rep. 1997; 14: 43
    • 1c Ward RS. Nat. Prod. Rep. 1999; 16: 75
    • 2a Kang MH, Naito M, Sakai K, Uchida K, Osawa T. Life Sci. 2000; 66: 161
    • 2b Kang MH, Katsuzaki H, Osawa T. Lipids 1998; 33: 1031
    • 2c Chiung YM, Hayashi H, Matsumoto H, Otani T, Yoshida K, Huang MY, Chen RX, Liu JR, Nakayama M. J. Antibiot. 1994; 47: 487
    • 2d Iwakami S, Wu JB, Ebizuka Y, Sankawa U. Chem. Pharm. Bull. 1992; 40: 1196
    • 2e Iwakami S, Ebizuka Y, Sankawa U. Heterocycles 1990; 30: 795
    • 2f Ichikawa K, Kinoshita T, Nishibe S, Sankawa U. Chem. Pharm. Bull. 1986; 34: 3514

      For our investigations on probe molecules, see:
    • 3a Ikeuchi K, Fujii R, Sugiyama S, Asakawa T, Inai M, Hamashima Y, Choi J.-H, Suzuki T, Kawagishi H, Kan T. Org. Biomol. Chem. 2014; 12: 3813
    • 3b Hiza A, Tsukaguchi Y, Ogawa T, Inai M, Asakawa T, Hamashima Y, Kan T. Heterocycles 2013; 88: 1371
    • 3c Sasaki S, Suzuki H, Ouchi H, Asakawa T, Inai M, Sakai R, Shimamoto K, Hamashima Y, Kan T. Org. Lett. 2014; 16: 564
    • 3d Yoshida A, Hirooka Y, Sugata Y, Nitta M, Manabe T, Ido S, Murakami K, Saha RK, Suzuki T, Ohshima M, Yoshida A, Itoh K, Shimizu K, Oku N, Furuta T, Asakawa T, Wakimoto T, Kan T. Chem. Commun. 2011; 47: 1794
    • 3e Fuwa H, Takahashi Y, Konno Y, Watanabe N, Miyashita H, Sasaki M, Natsugari H, Kan T, Fukuyama T, Tomita T, Iwatsubo T. ACS Chem. Biol. 2007; 2: 408
    • 3f Kan T, Kita Y, Morohashi Y, Tominari Y, Hosoda S, Tomita T, Natsugari H, Iwatsubo T, Fukuyama T. Org. Lett. 2007; 9: 2055
    • 3g Morohashi Y, Kan T, Tominari Y, Fuwa H, Okamura Y, Watanabe N, Natsugari H, Fukuyama T, Iwatsubo T, Tomita T. J. Biol. Chem. 2006; 281: 14670
    • 3h Kan T, Tominari Y, Morohashi Y, Natsugari H, Tomita T, Iwatsubo T, Fukuyama T. Chem. Commun. 2003; 2244

      For selected examples:
    • 4a Kim J.-C, Kim K.-H, Jung J.-C, Park O.-S. Tetrahedron: Asymmetry 2006; 17: 3
    • 4b Aldous DJ, Batsanov AS, Yufit DS, Dalençon AJ, Dutton WM, Steel PG. Org. Biomol. Chem. 2006; 4: 2912
    • 4c Banerjee B, Roy SC. Synthesis 2005; 2913
    • 4d Kise N, Fujimoto A, Moriyama N, Ueda N. Tetrahedron: Asymmetry 2003; 14: 2495
    • 4e Brown RC. D, Bataille CJ. R, Bruton G, Hinks JD, Swain NA. J. Org. Chem. 2001; 66: 6719
    • 4f Rana KK, Guin C, Roy SC. Tetrahedron Lett. 2000; 41: 9337
    • 4g Hull HM, Jones RG, Knight DW. J. Chem. Soc., Perkin Trans. 1 1998; 1779
    • 4h Samizu K, Ogasawara K. Chem. Lett. 1995; 543
    • 4i Suginome H, Orito K, Yorita K, Ishikawa M, Shimoyama N, Sasaki T. J. Org. Chem. 1995; 60: 3052
    • 4j Orito K, Yorita K, Suginome H. Tetrahedron Lett. 1991; 32: 5999
    • 4k Takano S, Ohkawa T, Tamori S, Satoh S, Ogasawara K. J. Chem. Soc., Chem. Commun. 1988; 189
    • 4l Pelter A, Ward RS, Watson DJ, Jack IR. J. Chem. Soc., Perkin Trans. 1 1982; 183
    • 4m Pelter A, Ward RS, Watson DJ, Collins P, Kay IT. J. Chem. Soc., Perkin Trans. 1 1982; 175
    • 4n Beroza M, Schechter MS. J. Am. Chem. Soc. 1956; 78: 1242
    • 5a Aldous DJ, Batsanov AS, Yufit DS, Dalencon AJ, Dutton WM, Steel PG. Org. Biomol. Chem. 2006; 4: 2912
    • 5b Swain NA, Brown RC. D, Bruton G. J. Org. Chem. 2004; 69: 122
    • 5c Roy SC, Rana KK, Guin C. J. Org. Chem. 2002; 67: 3242
    • 5d Brown RC. D, Bataille CJ. R, Bruton G, Hinks JD, Swain NA. J. Org. Chem. 2001; 66: 6719
    • 5e Ohmizu H, Ogiku T, Iwasaki T. Heterocycles 2000; 52: 1399
  • 6 We previously reported a part of this work as a communication, see: Ishikawa R, Yoshida N, Akao Y, Kawabe Y, Inai M, Asakawa T, Hamashima Y, Kan T. Chem. Lett. 2014; 43: 1572

    • For a short review, see:
    • 7a Asakawa T, Hamashima Y, Kan T. Curr. Pharm. Des. 2013; 19: 6207

    • See also:
    • 7b Furuta T, Hirooka Y, Abe A, Sugata Y, Ueda M, Murakami K, Suzuki T, Tanaka K, Kan T. Bioorg. Med. Chem. Lett. 2007; 17: 3095
    • 7c Hirooka Y, Nitta M, Furuta T, Kan T. Synlett 2008; 3234
    • 7d Aihara Y, Yoshida A, Furuta T, Wakimoto T, Akizawa T, Konishi M, Kan T. Bioorg. Med. Chem. Lett. 2009; 19: 4171
    • 7e Kawabe Y, Aihara Y, Hirose Y, Sakurada A, Yoshida A, Inai M, Asakawa T, Hamashima Y, Kan T. Synlett 2013; 24: 479
  • 8 Kawabe Y, Ishikawa R, Akao Y, Yoshida A, Inai M, Asakawa T, Hamashima Y, Kan T. Org. Lett. 2014; 16: 1976
    • 9a Chi Y, Gellman SH. J. Am. Chem. Soc. 2006; 128: 6804
    • 9b Freeman PT, Siggel L, Chamberlain PH. Tetrahedron 1988; 44: 5051

      Hajra and co-workers reported a similar aldol reaction, but they noted that reactions with electron-rich benzaldehydes were difficult, see:
    • 10a Hajra S, Giri AK. J. Org. Chem. 2008; 73: 3935
    • 10b Northrup AB, MacMillan DW. C. J. Am. Chem. Soc. 2002; 124: 6798

      For protection of phenols, see references 7d and 7e. For reviews on Ns chemistry, see:
    • 11a Kan T, Fukuyama T. Chem. Commun. 2004; 353
    • 11b Kan T, Fukuyama T. J. Synth. Org. Chem., Jpn. 2001; 59: 779
  • 12 Poe SL, Bogdan AR, Mason BP, Steinbacher JL, Opalka SM, McQuade DT. J. Org. Chem. 2009; 74: 1574
    • 13a Shimokawa J, Harada T, Yokoshima S, Fukuyama T. J. Am. Chem. Soc. 2011; 133: 17634
    • 13b Soai K, Oyamada H, Takase M, Ookawa A. Bull. Chem. Soc. Jpn. 1984; 57: 1948
    • 14a Mori N, Watanabe H, Kitahara T. Synthesis 2006; 400
    • 14b Matsui M, Miyano M, Tomita K. Bull. Agric. Chem. Soc. Jpn. 1956; 20: 139
    • 14c Kollonitsch J, Fuchs O, Gabor V. Nature 1954; 173: 125
  • 15 Brown and co-workers reported a total synthesis of (+)-methylpiperitol (1c), see reference 5d.
    • 16a Jan K.-C, Hwang LS, Ho C.-T. J. Agric. Food Chem. 2009; 57: 6101
    • 16b Jan K.-C, Ku K.-L, Chu Y.-H, Hwang LS, Ho C.-T. J. Agric. Food Chem. 2011; 59: 3078
    • 17a Banerjee B, Roy SC. Synthesis 2005; 2913
    • 17b Enders D, Lausberg V, Del SG, Berner OM. Synthesis 2002; 515
    • 17c Hoke M, Hansel R. Arch. Pharm. (Weinheim, Ger.) 1972; 33: 305
    • 17d Ogiku T, Yoshida S, Ohmizu H, Iwasaki T. J. Org. Chem. 1995; 60: 1148
    • 17e Pan J.-X, Hensens OD, Zink DL, Chang MN, Hwang S.-B. Phytochemistry 1987; 26: 1377
    • 17f Pelter A, Ward RS, Collins P, Venkateswarlu R, Kay IT. J. Chem. Soc., Perkin Trans. 1 1985; 587
    • 18a Iida T, Nakano M, Ito K. Phytochemistry 1982; 21: 673
    • 18b Latip J, Hartley TG, Waterman PG. Phytochemistry 1999; 51: 107
    • 18c Schmidt TJ, Hemmati S, Fuss E, Alfermann AW. Phytochem. Anal. 2006; 17: 299
  • 19 Maes D, Vervisch S, Debenedetti S, Davio C, Mangelinckx S, Giubellina N, De Kimpe N. Tetrahedron 2005; 61: 2505