First Total Synthesis of Cytotoxic Diarylheptanoids, Galeon, and Pterocarine

References

• Keserü , G. M. and Nógrádi , M. 1995 . “ The chemistry of natural diarylheptanoids ” . In Studies in Natural Products Chemistry Edited by: Atta‐ur‐Rahman . Vol. 17 , 357 – 394 . New York : Elsevier Science .
   Google Scholar
• Semmelhack , M. F. , Helquist , P. , Jones , L. D. , Keller , L. , Mendelson , L. , Ryono , L. S. , Smith , J. G. and Stauffer , R. D. 1981 . Reaction of aryl and vinyl halides with zerovalent nickel‐preparative aspects and the synthesis of alnusone . J. Am. Chem. Soc. , 103 : 6460 – 6471 . and references therein
   Web of Science ®Google Scholar
• Whiting , D. A. and Wood , A. F. 1978 . Cyclisation of 1,7‐diarylheptanoids through oxidative, reductive, and photochemical radical processes: Total syntheses of the m,m‐bridged biaryls myricanone and (±)‐myricanol, and a related diaryl ether . Tetrahedron Lett. , : 2335 – 2338 .
   Google Scholar
• Whiting , D. A. and Wood , A. F. 1980 . Total syntheses of the meta, meta‐bridged biphenyls (±)‐myricanol and myricanone, and of an isomeric biphenyl ether, a 14‐oxa[7,1]meta‐paracyclophane . J. Chem. Soc., Perkin Trans. 1 , : 623 – 628 .
   Google Scholar
• Vermes , B. , Keserü , G. , Mezey‐Vándor , G. , Nógrádi , M. and Tóth , G. 1993 . The synthesis of garugamblin‐1 . Tetrahedron , 49 : 4893 – 4900 . and references therein
   Google Scholar
• Huang , M.‐T. , Lysz , T. , Ferraro , T. , Abidi , T. F. , Laskin , J. D. and Conney , A. H. 1991 . Inhibitory effects of curcumin on in vitro lipoxygenase and cyclooxygenase activities in mouse epidermis . Cancer Res. , 51 : 813 – 819 .
   PubMed Web of Science ®Google Scholar
• Lee , S.‐L. , Huang , W.‐J. , Lin , W. W. , Lee , S.‐S. and Chen , C.‐H. 2005 . Preparation and anti‐ inflammatory activities of diarylheptanoid and diarylheptylamine analogs . Bioorg. Med. Chem. , 13 : 6175 – 6181 .
   PubMed Web of Science ®Google Scholar
• Weber , W. M. , Hunsaker , L. A. , Deck , L. M. and Vander Jagt , D. L. Synthesis of enone analogues of the natural product curcumin . 230th ACS National Meeting, American Chemical Society . Aug. 28–Sept. 1 , Washington, DC, United States. pp. MEDI‐149 Abstracts of Papers
   Google Scholar
• Selvam , C. , Jachak , S. M. , Thilagavathi , R. and Chakraborti , A. K. 2005 . Design, synthesis, biological evaluation and molecular docking of curcumin analogues as antioxidant, cyclooxygenase inhibitory and anti‐inflammatory agents . Bioorg. Med. Chem. Lett. , 15 : 1793 – 1797 .
   PubMed Web of Science ®Google Scholar
• Schraufstatter , E. and Bernt , H. 1949 . Antibacterial action of curcumin and related compounds . Nature (London) , 164 : 456 – 457 .
   PubMed Web of Science ®Google Scholar
• Jovanovic , S. V. , Steenken , S. , Boone , C. W. and Simic , G. 1999 . H‐atom transfer is a preferred antioxidant mechanism of curcumin . J. Am. Chem. Soc. , 121 : 9677 – 9681 .
   Web of Science ®Google Scholar
• Barclay , L. R. C. , Vinqvist , M. R. , Kazuo Mukai , K. , Goto , H. , Hashimoto , Y. , Tokunaga , A. and Uno , H. 2000 . On the antioxidant mechanism of curcumin: Classical methods are needed to determine antioxidant mechanism and activity . Org. Lett. , 2 : 2841 – 2843 .
   PubMed Web of Science ®Google Scholar
• Huang , M.‐T. , Smart , R. C. , Wong , C.‐Q. and Conney , A. H. 1988 . Inhibitory effect of curcumin, chlorogenic acid, caffeic acid and ferulic acid on tumor promotion in mouse skin by 12‐O‐tetradecanoylphorbol‐13‐acetate . Cancer Res. , 48 : 5941 – 5946 . For curcumins
   PubMed Web of Science ®Google Scholar
• Liu , J.‐Y. , Lin , S.‐J. and Lin , J.‐K. 1993 . Inhibitory effects of curcumin on protein kinase C activity induced by 12‐O‐tetradecanoylphorbol‐13‐acetate in NIH 3T3 cells . Carcinogenesis , 14 : 857 – 861 .
   PubMed Web of Science ®Google Scholar
• Ruby , A. J. , Kuttan , G. , Babu , K. D. , Rajasekharan , K. N. and Kuttan , R. 1995 . Anti‐tumor and antioxidant activity of natural curcuminoids . Cancer Lett. , 94 : 79 – 83 .
   PubMed Web of Science ®Google Scholar
• Ishida , J. , Kozuka , M. , Wang , H.‐K. , Konoshima , T. , Tokuda , H. , Okuda , M. , Yang Mou , X. , Nishino , H. , Sakurai , N. , Lee , K.‐H. and Nagai , M. 2000 . Antitumor‐promoting effects of cyclic diarylheptanoids on Epstein–Barr virus activation and two‐stage mouse skin carcinogenesis . Cancer Lett. , 159 : 135 – 140 . For biphenylheptaoids
   PubMed Web of Science ®Google Scholar
• Ishida , J. , Kozuka , M. , Tokuda , H. , Nishino , H. , Nagumo , S. , Lee , K.‐H. and Nagai , M. 2002 . Chemopreventive potential of cyclic diarylheptanoids . Bioorg. Med. Chem. , 10 : 3361 – 3365 .
   PubMed Web of Science ®Google Scholar
• Morikawa , T. , Tao , J. , Toguchida , I. , Matsuda , H. and Yoshikawa , M. 2003 . Structure of new cyclic diarylheptanoids and inhibitors of nitric oxide production from Japanese folk medicine Acer nikoense . J. Nat. Prod. , 66 : 86 – 91 .
   PubMed Web of Science ®Google Scholar
• Kang , H.‐M. , Son , K.‐H. , Yang , D. C. , Han , D.‐C. , Kim , J. H. , Baek , N.‐I. and Kwon , B.‐M. 2004 . Inhibitory activity of diarylheptanoids on farnesyl protein transferase . Nat. Prod. Res. , 18 : 295 – 299 .
   PubMed Web of Science ®Google Scholar
• Nagai , M. , Kubo , M. , Fujita , M. , Inoue , T. and Matsuo , M. 1976 . Acerogenin A, a novel cyclic diarylheptanoid . Chem. Commun. , : 338 – 339 .
   Google Scholar
• Nagai , M. , Kubo , M. , Fujita , M. , Inoue , T. and Matsuo , M. 1978 . Studies on the constituents of Aceroceae plants, II: Structure of aceroside I, a glucoside of a novel cyclic diarylheptanoid from Acer nikoense Maxim . Chem. Pharm. Bull. , 26 : 2805 – 2810 .
   Google Scholar
• Kubo , M. , Inoue , T. and Nagai , M. 1980 . Studies on the constituents of aceroceae plants, III: Structure of acerogenin B from Acer nikoense Maxim . Chem. Pharm. Bull. , 28 : 1300 – 1303 .
   Google Scholar
• Kubo , M. , Nagai , M. and Inoue , T. 1983 . Studies on the constituents of Aceroceae plants, IV: Carbon‐13 nuclear magnetic resonance spectra of acerogenin A, rhododendrol, and related compounds, and structure of aceroside IV from Acer nikoense . Chem. Pharm. Bull. , 31 : 1917 – 1922 .
   Google Scholar
• Nagai , M. , Kubo , M. , Takahashi , K. , Fujita , M. and Inoue , T. 1983 . Studies on the constituents of Aceraceae plants, V: Two diarylheptanoid glycosides and an arylbutanol apiosylglucoside from Acer nikoense . Chem. Pharm. Bull. , 31 : 1923 – 1928 .
   Google Scholar
• Nagai , M. , Kenmochi , N. , Fujita , M. , Furukawa , N. and Inoue , T. 1986 . Studies on the constituents of Aceraceae plants, VI: Revised stereochemistry of (‐)‐centrolobol, and new glycosides from Acer nikoense . Chem. Pharm. Bull. , 34 : 1056 – 1060 .
   Web of Science ®Google Scholar
• Nagumo , S. , Kaji , N. , Inoue , T. and Nagai , M. 1993 . Studies on the constituents of Aceraceae plants, XI: Two types of cyclic diarylheptanoid from Acer nikoense . Chem. Pharm. Bull. , 41 : 1255 – 1257 .
   Google Scholar
• Malterud , K. E. , Anthonsen , T. and Hjortas , J. 1976 . 14‐Oxa‐[7.1]metaparacyclophanes from Myrica gale L., a new class of natural products . Tetrahedron Lett. , 35 : 3069 – 3070 .
   Google Scholar
• Morihara , M. , Sakurai , N. , Inoue , T. , Kawai , K.‐I. and Nagai , M. 1997 . Two novel diarylheptanoid glucosides from Myrica gale var. tomentosa and absolute structure of plane‐chiral galeon . Chem. Pharm. Bull. , 45 : 820 – 823 .
   Web of Science ®Google Scholar
• Liu , H. B. , Cui , C. B. , Cai , B. , Gu , Q. Q. , Zhang , D. Y. , Zhao , Q. C. and Guan , H. S. 2005 . Pterocarine, a new diarylheptanoid from Pterocaria tonkinesis, its cell cycle inhibition at G0/G1 phase and induction of apoptosis in HCT‐15 and K562 cells . Chin. Chem. Lett. , 16 : 215 – 218 .
   Web of Science ®Google Scholar
• Isalas Gonzalez , G. and Zhu , J. 1997 . First total synthesis of acerogenin C and aceroside IV . J. Org. Chem. , 62 : 7544 – 7545 .
   Google Scholar
• Isalas Gonzalez , G. and Zhu , J. 1999 . A unified strategy toward the synthesis of acerogenin‐type macrocycles: Total syntheses of acerogenin A, B, C, and L and aceroside IV . J. Org. Chem. , 64 : 914 – 924 .
   PubMedGoogle Scholar
• Keserü , G. M. , Nógródi , M. and Szöllösy , A. 1998 . Synthesis of acerogenin C and (+)‐acerogenin A, two macrocyclic diarylheptanoids constituents of Acer nikoense . Eur. J. Org. Chem. , : 521 – 524 .
   Google Scholar
• Lee , K.‐S. , Li , G. , Kim , S. H. , Lee , J.‐S. , Woo , M.‐H. , Lee , S.‐H. , Jahng , Y. and Son , J. K. 2002 . Cytotoxic diarylheptanoids from the roots of Juglans mandshurica . J. Nat. Prod. , 65 : 1707 – 1708 .
   PubMed Web of Science ®Google Scholar
• Locksley , H. D. , Rainey , D. K. and Rohan , T. A. 1972 . Bush pungent compounds, part I: An improved synthesis of the paradols (alkyl 4‐hydroxy‐3‐methoxyphenethyl ketones) and an assessment of their pungency . J. Chem. Soc., Perkin Trans. 1 , : 3001 – 3006 .
   Google Scholar
• Itokawa , H. , Aiyama , R. and Ikuta , A. 1983 . Synthesis of diarylheptanoids and assessment of their pungency . Chem. Pharm. Bull. , 31 : 2491 – 2496 .
   Web of Science ®Google Scholar
• Sawyer , J. S. 2000 . Recent advances in diaryl ether synthesis . Tetrahedron , 56 : 5045 – 5065 . For a review based on the reaction mechanism, see
   Web of Science ®Google Scholar
• Lindley , J. 1984 . Copper assisted nucleophilic substitution of aryl halogen . Tetrahedron , 40 : 1433 – 1456 . For a review for the classical Ullmann reaction condition, see
   Web of Science ®Google Scholar
• Evans , D. A. and Ellman , J. A. 1989 . The total syntheses of the isodityrosine‐derived cyclic tripeptides OF4949‐I11 and K‐13: Determination of the absolute configuration of K‐13 . J. Am. Chem. Soc. , 111 : 1063 – 1072 .
   Web of Science ®Google Scholar