Improved Synthesis of L,L-Cycloisodityrosine Subunit of Antitumor Agents Deoxybouvardin and RA-VII

REFERENCES

• Jolad , S. D. ; Hoffmann , J. J. ; Torrance , S. J. ; Wiedhopf , R. M. ; Cole , J. R. ; Arora , S. K. ; Bates , R. B. ; Gargiulo , R. L. ; Kriek , G. R. Bouvardin and deoxybouvardin, antitumor cyclic hexapeptides from Bouvardia ternifolia (Rubiaceae) . J. Am. Chem. Soc. 1977 , 99 , 8040 .
   PubMed Web of Science ®Google Scholar
• Itokawa , H. ; Takeya , K. ; Mori , N. ; Sonobe , T. ; Mihashi , S. ; Ha manaka , T. Studies on antitumor cyclic hexapeptides RA obtained from Rubiae radix, Rubiaceae, VI: Minor antitumor constituents . Chem. Pharm. Bull. 1986 , 34 , 3762 .
   PubMed Web of Science ®Google Scholar
• Rama Rao , A. V. ; Gurjar , M. K. ; Reddy , K. L. ; Rao , A. S. Studies directed toward the synthesis of vancomycin and related cyclic peptides . Chem. Rev. 1995 , 95 , 2135 – 2167 .
   Web of Science ®Google Scholar
• Boger , D. L. ; Yohannes , D. Total synthesis of deoxybouvardin and RA-VII: Macrocyclization via an intramolecular Ullmann reaction . J. Am. Chem. Soc. 1991 , 113 , 1427 – 1429 .
   Web of Science ®Google Scholar
• Inaba , T. ; Umezawa , I. ; Yuasa , M. ; Inoue , T. ; Mihashi , S. ; Itokawa , H. ; Ogura , K. The first total synthesis of deoxybouvardin and RA-VII, novel antitumor cyclic hexapeptides . J. Org. Chem. 1987 , 52 , 2957 – 2958 .
   Web of Science ®Google Scholar
• Boger , D. L. ; Patane , M. A. ; Jin , Q. ; Kitos , P. A. Design, synthesis, and evaluation of bouvardin, deoxybouvardin, and RA-I-XIV pharmacophore analogs . Biorg. Med. Chem. 1994 , 2 , 85 – 100 .
   PubMedGoogle Scholar
• Boger , D. L. ; Yohannes , D. Studies on the total synthesis of bouvardin and deoxybouvardin: Cyclic hexapeptide cyclization studies and preparation of key partial structures. J. Org. Chem. 1988, 53, 487–499.
   Google Scholar
• Beugelmans , R. ; Bigot , A. ; Bois-Choussy , M. ; Zhu , J. A new approach to the synthesis of piperazinomycin and bouvardin: Facile access to cycloisodityrosine via an intramolecular SNAr reaction . J. Org. Chem. 1996 , 61 , 771 – 774 .
   PubMed Web of Science ®Google Scholar
• Poupardin , O. ; Ferreira , F. ; Genet , J. P.; Greck C. Synthesis of (+)-testudinariol A, a triterpene metabolite of the marine mollusc Pleurobrancus testudinarius . Tetrahedron Lett. 2001 , 42 , 1523 – 1526 .
   Google Scholar
• Hitotsuyanagi , Y. ; Hasuda , T. ; Matsumoto , Y. ; Yamaguchi , K. ; Itokawa , H. ; Takeya , K. Degradation of an antitumour bicyclic hexapeptide RA-VII into cycloisodityrosines . Chem. Commun. 2000 , 1633 – 1634 .
   Google Scholar
• Chan , D. M. T. ; Monaco , K. L. ; Wang , R.-P. ; Winters , M. P. New N- and O-arylations with phenylboronic acids and cupric acetate . Tetrahedron Lett. 1998 , 39 , 2933 – 2936 .
   Web of Science ®Google Scholar
• Evans , D. A. ; Katz , J. L. ; West , T. R. Synthesis of diaryl ethers through the copper-promoted arylation of phenols with arylboronic acids: An expedient synthesis of thyroxine . Tetrahedron Lett. 1998 , 39 , 2937 – 2940 .
   Web of Science ®Google Scholar
• Lam , P. Y. S. ; Clark , C. G. ; Saubern , S. ; Adams , J. ; Winters , M. P. ; Chan , D. M. T. ; Combs , A. New aryl/heteroaryl C—N bond cross-coupling reactions via arylboronic acid/cupric acetate arylation . Tetrahedron Lett. 1998 , 39 , 2941 – 2944 .
   Web of Science ®Google Scholar
• Hitotsuyanagi , Y. ; Ishikawa , H. ; Naito , S. ; Takeya , K. Synthesis of L,L-cycloisodityrosines by copper(II) acetate-DMAP-mediated intramolecular O-arylation of phenols with phenylboronic acids . Tetrahedron Lett. 2003 , 44 , 5901 – 5903 .
   Web of Science ®Google Scholar