Straightforward and Facile Approach Toward the N-Derivatization of Pyroglutamates Through Mitsunobu Reaction: Synthesis of N-Alkyl/N-Acyl Pyroglutamates

REFERENCES

• Peterson , J. S. ; Fels , G. ; Rapoport , H. Chirospecific synthesis of (+) and (−)-anatoxin a . J. Am. Chem. Soc. 1984 , 106 , 4539 – 4547 .
   Web of Science ®Google Scholar
• Panday , S. K. ; Langlois , N. An efficient straight forward synthesis of (−)-bulgecinine . Synth. Commun. 1997 , 27 ( 8 ), 1373 – 1384 .
   Web of Science ®Google Scholar
• Caubert , V. ; Masse , J. ; Retailleau , P. ; Langlois , N. Stereoselective formal synthesis of the potent proteasome inhibitors: Salinosporamide A. Tetrahedron Lett . 2007, 48, 381–384 and references cited theirin.
   Web of Science ®Google Scholar
• Imaki , K. ; Sakuyama , S. ; Okada , T. ; Toda , M. ; Hayashi , M. ; Miyamoto , T. ; Kawasaki , A. ; Okegawa , T. Potent orally active inhibitors of angiotensin-converting enzyme (ACE) . Chem. Pharm. Bull 1981 , 29 , 2210 – 2214 .
   PubMed Web of Science ®Google Scholar
• Panday , S. K. ; Dikshit , M. ; Dikshit , D. K. Synthesis of N-[30-(acetylthio)alkanoyl] and N-[30-mercaptoalkanoyl]-4-a(s)-(phenylmethyl) pyroglutamic acids and prolines as potent ACE inhibitors . Med. Chem. Res. 2009 , 18 , 566 – 578 .
   Google Scholar
• Thaisrivongs , S. ; Pals , D. T. ; Turner , S. R. ; Kroll , L. T. Conformationally constrained rennin inhibitory peptides: Gammalactam-bridged dipeptide isostere as conformational restriction . J. Med. Chem. 1988 , 31 , 1369 – 1376 .
   PubMed Web of Science ®Google Scholar
• Yu , K. L. ; Rajakumar , G. ; Srivastava , L. K. ; Mishra , R. K. ; Johnson , R. L. Dopamine receptor modulation by conformationally constrained analogues of Pro-Leu-gly-NH2 . J. Med. Chem. 1988 , 31 , 1430 – 1436 .
   PubMedGoogle Scholar
• Stevens , C. V. ; Rammeloo , T. ; Kimpe , N. D. Directing the resioselectivity of the alkylation of pyroglutamates carbamates by formation of a stable counter-ion complex . Synlett. 2001 , 10 , 1519 – 1522 .
   Google Scholar
• Dikshit , D. K. ; Maheshwari , A. ; Panday , S. K. Self-reproduction of chirality in pyroglutamates: Reactions at α-position with electrophiles . Tetrahedron Lett. 1995 , 36 , 6131 – 6134 .
   Web of Science ®Google Scholar
• Herdeis , C. ; Kelm , B. A stereoselective synthesis of 3-substituted(S)-pyroglutamic and glutamic acids via OBO ester derivatives . Tetrahedron 2003 , 59 , 217 – 219 .
   Google Scholar
• Dikshit , D. K. ; Panday , S. K. Aldol reactions of pyroglutamates: Chiral synthesis of 4-α (S)-and 4-β(R)-arylmethyl pyroglutamates . J. Org. Chem. 1992 , 57 , 1920 – 1924 .
   Google Scholar
• Dieltiens , N. ; Stevens , C. V. ; Masschelein , K. G. R. ; Rommeloo , T. [1,2] Boc migration during pyroglutamate alkylations . Tetrahedron 2005 , 61 , 6749 – 6756 and references cited their in .
   Google Scholar
• Hussaini , S. R. ; Moloney , M. G. 2,5-Disubstituted pyrrolidines: Synthesis by enamine reduction and subsequent regioselective and diastereoselective alkylations . Org. Biomol. Chem. 2006 , 4 , 2600 – 2615 .
   Google Scholar
• Hussaini , S. R. ; Moloney , M. G. CIS-selective synthesis of 2,5-disubstituted pyrrolidines . Tetrahedron Lett. 2004 , 45 , 1125 – 1127 .
   Google Scholar
• Agarwal , V. K. ; Astle , C. J. ; Iding , H. ; Werz , B. ; Evans , M. R. Separation of pyrrolidines allylation products by diastereoselective enzymatic hydrolysis . Tetrahedron Lett. 2005 , 46 , 945 – 947 .
   Google Scholar
• Bourry , A. ; Rigo , B. ; Sanz , G. ; Couturier , D. Studies on pyrrolidinones: Some attempts to improve the anticancer properties of methyl N-(3,4,4′,5-tetramethoxybenzhydryl) pyroglutamate (HEI81) . J. Heterocyclic Chem. 2002 , 39 , 119 – 124 and references cited their in .
   Google Scholar
• Krapcho , J. ; Turk , C. ; Cushman , D. W. ; Powell , J. R. ; Deforrest , J. M. ; Spitzmiller , E. R. ; Karanewsky , D. S. ; Duggan , M. ; Rovnyak , G. ; Schwartz , J. ; Natrajan , S. ; Godfrey , J. D. ; Ryono , D. E. ; Neubeck , R. ; Atwal , K. S. ; Petrillo , E. W. Jr. Angiotensin-converting enzyme inhibitors, mercaptan, carboxyalkyl dipeptide and phosphinic acid inhibitors incorporating 4-substituted prolines . J. Med. Chem. 1988 , 31 ( 6 ), 1148 – 1160 .
   PubMed Web of Science ®Google Scholar
• Smith , E. M. ; Swiss , G. F. ; Neustadt , B. R. ; McNamara , P. ; Gold , E. H. ; Sybertz , E. J. ; Baum , T. Angiotensin converting enzyme inhibitors: spirapril and related compounds . J. Med. Chem. 1989 , 32 , 1600 – 1606 .
   PubMed Web of Science ®Google Scholar
• Smith , E. M. ; Swiss , G. F. ; Neustadt , B. R. ; Gold , E. H. ; Sommer , J. A. ; Brown , A. D. ; Chiu , P. J. S. ; Moran , R. ; Sybertz , E. J. ; Baum , T. J. Synthesis and pharmacological activity of angiotensin-converting enzyme inhibitors: N-(Mercaptoalkanoyl)-4-substituted-(S)-prolines . J. Med. Chem. 1988 , 31 ( 4 ), 875 – 885 .
   Google Scholar
• Thottahil , J. K. ; Moniot , J. L. ; Mueller , R. H. ; Wong , M. K. Y. ; Kissick , T. P. J. Conversion of L-pyroglutamic acid to 4-alkyl substituted-L-prolines: The synthesis of trans-4-cyclohexyl-L-proline. J. Org. Chem. 1986, 51, 3140–3143.
   Google Scholar
• Panday , S. K. ; Prasad , J. ; Dikshit , D. K. Pyroglutamic acid: A unique chiral synthon . Tetrahedron Asymmetry 2009 , 20 , 1581 – 1632 and references sited therein .
   Google Scholar
• Rigo , B. ; Lespagnol , C. ; Pauly , M. Studies on pyrrolidinones: Synthesis of N-acyl pyroglutamic esters with bactericide and fungicide properties . J. Heterocycl. Chem. 1988 , 25 ( 1 ), 49 – 59 .
   Google Scholar
• Hughes , D. L. The Mitsunobu Reaction . Org. React. 1992 , 42 , 335 – 656 .
   Web of Science ®Google Scholar
• But , T. Y. S. ; Toy , P. H. Organocatalytic mitsunobu reaction . J. Am. Chem. Soc. 2006 , 128 , 9636 – 9637 and references cited there in .
   PubMed Web of Science ®Google Scholar
• Lepore , S. D. ; He , Y. Use of sonication for the coupling of sterically hindered substrates in the phenolic Mitsunobu reaction . J. Org. Chem. 2003 , 68 , 8261 – 8263 .
   PubMed Web of Science ®Google Scholar
• Olofsson , B. ; Wijtmans , R. ; Somfai , P. Synthesis of N-H vinylaziridines: A comparative study . Tetrahedron 2002 , 58 , 5979 – 5982 .
   Google Scholar
• Sen , S. E. ; Roach , S. L. A convenient two - step procedure for the synthesis allylic amines from allylic alcohols . Synthesis 1995 , 756 – 758 .
   Google Scholar
• Mavromoustakos , T. ; Minakakis , P. M. ; Kokotos , C. G. ; Kontogianni , P. ; Politi , A. ; Zoumpoulakis , P. ; Findlay , J. ; Cox , A. ; Balmforth , A. ; Zoga , A. ; Iliodromitis , E. Synthesis, binding studies, and in vivo biological evaluation of novel nonpeptide antihypertensive analogues . Bioorg. Med. Chem. 2006 , 14 , 4353 – 4360 .
   PubMed Web of Science ®Google Scholar