Synthesis of the Southern Tripeptide (C₁–N₁₂) of Sanglifehrins Using Asymmetric Organocatalysis

REFERENCES

• (a) For cyclophilin binding of cyclosporin A, see Handschumacher , R. E. ; Harding , M. W. ; Rice , J. ; Drugge , R. J. ; Speicher , D. W. Science. 1984 , 226 , 544 – 547 ; (b) for FK BP binding of FK 506 and rapamycin , see Siekierka , J. J. ; Hung , S. H. Y. ; Poe , M. ; Lin , C. S. ; Sigal , N. H. Nature. 1989 , 341 , 755 – 757 .
   PubMed Web of Science ®Google Scholar
• (a) Sanglier , J. J. ; Quesniaux , V. ; Fehr , T. ; Hofmann , H. ; Mahnke , M. ; Memmert , K. ; Schuler , W. ; Zenke , G. ; Gschwind , L. ; Maurer , C. ; Schilling , W. ; J. Antibiot. 1999, 52, 466–473; (b) Fehr , T. ; Kallen , J. ; Oberer , L. ; Sanglier , J. J. ; Schilling , W. J. Antibiot. 1999, 52, 474–479.
   PubMed Web of Science ®Google Scholar
• Kallen , J. ; Sedrani , R. ; Zenke , G. ; Wagner , J. J. Biol. Chem. 2005 , 280 ( 23 ), 21965 – 21971 .
   PubMed Web of Science ®Google Scholar
• Zhang , L. H. ; Liu , J. O. J. Immunol. 2001 , 166 , 5611 – 5618 .
   PubMed Web of Science ®Google Scholar
• (a) Nicolaou , K. C. ; Murphy , F. ; Barluenga , S. ; Ohshima , T. ; Wei , H. ; Xu , J. ; Gray , D. L. F. ; Baudoin , O. J. Am. Chem. Soc. 2000 , 122 , 3830 – 3838 ; (b) Paquette , L. A. ; Duan , M. ; Konetzki , I. ; Kempmann , C. J. Am. Chem. Soc. 2002 , 124 , 4257 – 4270 .
   Web of Science ®Google Scholar
• (a) Nicolaou , K. C. ; Ohshima , T. ; Murphy , F. ; Barluenga , S. ; Xu , J. ; Winssinger , N. Chem. Commun. 1999 , 809 – 810 ; (b) Nicolaou , K. C. ; Xu , J. ; Murphy , F. ; Barluenga , S. ; Baudoin , O. ; Wei , H.-X. ; Gray , D. L. F. ; Ohshima , T. Angew. Chem. Int. Ed. 1999 , 38 , 2447 – 2451 ; (c) Paquette , L. A. ; Konetzki , I. ; Duan , M. Tetrahedron Lett. 1999 , 40 , 7441 – 7444 ; (d) Duan , M. ; Paquette , L. A. Tetrahedron. Lett. 2000 , 41 , 3789 – 3792 ; (e) Duan , M. ; Paquette , L. A. Angew. Chem. Int. Ed. 2001 , 40 , 3632 – 3636 ; (f) Cabrejas , L. M. M. ; Rohrbach , S. ; Wagner , D. ; Kallen , J. ; Zenke , G. ; Wagner , J. Angew. Chem. Int. Ed. 1999 , 38 , 2443 – 2446 ; (g) Banteli , R. ; Brun , L. ; Hall , P. ; Metternich , R. Tetrahedron Lett. 1999 , 40 , 2109 – 2112 ; (h) Metternich , R. ; Denni , D. ; Thai , B. ; Sedrani , R. J. Org. Chem. 1999 , 64 , 9632 – 9639 ; (i) Wagner , J. ; Cabrejas , L. M. M. ; Grossmith , C. M. ; Papageorgiou , C. ; Senia , F. ; Wagner , D. ; France , J. ; Nolan , S. P. J. Org. Chem. 2000 , 65 , 9255 – 9260 ; (j) Hall , P. ; Brun , J. ; Denni , D. ; Metternich , R. Synlett. 2000 , 315 – 318 ; (k) Gurjar , M. K. ; Chaudhuri , S. R. Tetrahedron Lett. 2002 , 43 , 2435 – 2438 ; (l) Sedrani , R. ; Kallen , J. ; Cabrejas , L. M. M. ; Papageorgiou , C. D. ; Senia , F. ; Rohrbach , S. ; Wagner , D. ; Thai , B. ; Eme , A. M. J. ; France , J. ; Oberer , L. ; Rihs , G. ; Zenke , G. ; Wagner , J. J. Am. Chem. Soc. 2003 , 125 , 3849 – 3859 ; (m) Dias , L. C. ; Salles Jr. , A. G. Tetrahedron Lett. 2006 , 47 , 2213 – 2216 ; (n) White , J. D. ; Suttisintong , K. J. Org. Chem. 2013 , 78 , 2757 – 2762 ; (o) Yadav , J. S. ; Raghavendra Rao , K. V. ; Kavitha , A. ; Mohapatra , D. K. Eur. J. Org. Chem. 2013 , 2849 – 2858 .
   Google Scholar
• (a) Bevan , K. ; Davies , J. S. ; Hassall , C. H. ; Morton , R. B. ; Phillips , D. A. S. J. Chem. Soc. 1971 , 514 – 522 (b) Hassall , C. H. ; Johnson , W. H. ; Theobald , C. J. J. Chem. Soc. Perkin Trans. 1. 1979 , 1451 – 1458 .
   Web of Science ®Google Scholar
• Bender , D. M. ; Williams , R. M. J. Org. Chem. 1997 , 62 , 6690 – 6691 .
   Web of Science ®Google Scholar
• (a) Chandrasekhar , S. ; Kavitha , N. ; Kumar , V. P. Tetrahedron Lett. 2013 , 54 , 2128 – 2130 ; (b) Chandrasekhar , S. ; Satish , K. ; Reddy , G. P. K. ; Mainkar , P. S. Tetrahedron: Asymmetry. 2011 , 22 , 1568 – 1573 ; (c) Chandrasekhar , S. ; Mahipal , B. ; Kavitha , M. J. Org. Chem. 2009 , 74 , 9531 – 9534 (d) Chandrasekhar , S. ; Lohitha Rao , Ch. ; Seenaiah , M. ; Naresh , P. ; Jagadeesh , B. ; Manjeera , D. ; Arpita , S. ; Bhadra , M. P. J. Org. Chem. 2009 , 74 , 401 – 404 ; (e) Chandrasekhar , S. ; Chandrasekhar , G. Tetrahedron: Asymmetry. 2005 , 16 , 2209 – 2214 ; (f) Chandrasekhar , S. ; Raza , A. ; Takhi , M. Tetrahedron: Asymmetry. 2002 , 13 , 423 – 428 .
   Web of Science ®Google Scholar
• Guanti , G. ; Banfi , L. ; Riva , R. Tetrahedron. 1994 , 50 ( 41 ), 11945 – 11966 .
   Web of Science ®Google Scholar
• For organocatalytic α-amination, see (a) List , B. J. Am. Chem. Soc. 2002 , 124 , 5656 – 5657 ; (b) Bogevig , A. ; Juhl , K. ; Kumaragurubaran , N. ; Zhuang , W. ; Jorgensen , K. A. Angew. Chem. Int. Ed. 2002 , 41 , 1790 – 1793 ; (c) Kumaragurubaran , N. ; Juhl , K. ; Zhuang , W. ; Bogevig , A. ; Jorgensen , K. A. J. Am. Chem. Soc. 2002 , 124 , 6254 – 6255 ; (d) Vogt , H. ; Vanderheiden , S. ; Brase , S. Chem. Commun. 2003 , 2448 – 2449 .
   PubMed Web of Science ®Google Scholar
• Enantiomeric excess was determined by chiral HPLC (CHIRAL PAK-IA; 250 × 4.6 mm, 5U, Mobile phase: 20% IPA in hexane, flow rate: 1 mL/min, detection: 210 nm; major tR 6.696 min, minor tR 17.432 min .
   Google Scholar
• (a) Kotkar , S. P. ; Sudalai , A. Tetrahedron: Asymmetry. 2006 , 17 , 1738 – 1742 ; (b) Udodong , U. E. ; Fraser-Reid , B. J. Org. Chem. 1989 , 54 , 2103 – 2112 .
   Web of Science ®Google Scholar
• Wang , W. ; Xiong , C. ; Zhang , J. ; Hruby , J. Tetrahedron. 2002, 58, 3101–3110.
   Web of Science ®Google Scholar
• Henmi , Y. ; Makino , K. ; Yoshitomi , Y. ; Harab , O. ; Hamada , Y. Tetrahedron: Asymmetry. 2004 , 15 , 3477 – 3480 .
   Web of Science ®Google Scholar
• Chen , Y. ; Lu , Y. ; Zou , Q. ; Chen , H. ; Ma , D. Org. Process Res. Dev. 2013 , 17 , 1209 – 1213 .
   Web of Science ®Google Scholar
• Enantiomeric excess of 12a was determined by chiral HPLC (CHIRALCEL-OD-H; 250 × 4.6 mm, 5U, mobile phase: 5% IPA in hexane, flow rate: 0.75 mL/min, minor tR 7.467 min, major tR 8.291 min .
   Google Scholar
• Diastereomeric excess was determined by HPLC analysis. Column: Atlantis dc18, 150 × 4.6, 5U; mobile phase: 60% ACN in H2O (0.1% FA); detection: 210 nm; flow rate: 1.0 mL/min; major isomer tR 9.23 min, minor isomer tR 9.71 min .
   Google Scholar
• Color versions of one or more of the figures in the article can be found online at www.tandfonline.com/lsyc.
   Google Scholar