Synthesis of Naphtho[2,1-b]pyrano Pyrrolothiazole Derivatives through 1,3-Cycloaddition Reaction

REFERENCES

• (a) Decosterd , L. A. ; Parsons , I. C. ; Gustafson , K. R. ; Cardellina II , J. H. ; McMahon , J. B. ; Cragg , G. M. ; Murata , Y. ; Pannell , L. K. ; Steiner , J. R. ; Clardy , J. ; Boyd , M. R. HIV inhibitory natural products, 11: Structure, absolute stereochemistry, and synthesis of conocurvone, a potent, novel HIV-inhibitory naphthoquinone trimer from a Conospermum sp . J. Am. Chem. Soc. 1993 , 115 , 6673 – 6679 ; (b) Bukuru , J. F. ; Van , T. N. ; Puyvelde , L. V. ; Mathenge , S. G. ; Mudida , F. P. ; Kimpe , N. D. A benzochromene from the roots of Pentas bussei . J. Nat. Prod. 2002 , 65 , 783 – 785 .
   Web of Science ®Google Scholar
• Gemert , B. V. Benzo and naphthopyrans (chromenes) ; In Organic Photochromic and Thermochromic Compounds ; J. C. Crano , R. Guglielmetti (Eds.); Plenum Press : New York , 1999 ; vol. 1 , chapter 3 .
   Google Scholar
• Roeder , E. Medicinal plants in Europe containing pyrrolizidine alkaloids . Pharmazie 1995 , 50 , 83 – 98 .
   PubMed Web of Science ®Google Scholar
• Hartmann , T. ; Witte , L. ; Ehmke , A. ; Theuring , C. ; Rowell-Rahier , M. ; Pasteels , J. M. Selective sequestration and metabolism of plant-derived pyrrolizidine alkaloids by chrysomelid leaf beetles . Phytochemistry 1997 , 45 , 489 – 497 .
   Web of Science ®Google Scholar
• (a) Hartmann , T. ; Witte , L. In Alkaloids: Chemical and Biological Perspectives ; S. W. Pelletier (Ed.); Pergamon Press : New York , 1995 ; chapter 4 , pp. 155 – 233 ; (b) Mattocks , A. R. Chemistry and Toxicology of Pyrrolizidine Alkaloids ; Academic Press : London , 1986 ; (c) Pereda-Miranda , R. In Phytochemistry of Medicinal Plants ; J. T. Arnason , R. Mata , J. T. Romeo (Eds.); Plennum Press : New York , 1995 ; chapter 5 , pp. 103 – 108 .
   Google Scholar
• (a) Gallos , J. K. ; Sarli , V. C. ; Koftis , T. V. ; Coutouli-Argyropoulou , E. A new entry to hydroxylated pyrrolizidines. Tetrahedron Lett. 2000, 41, 4819; (d) Denmark , S. E. ; Hurd , A. R. Nickel-mediated amination chemistry, part 1: Efficient aminations of (het)aryl 1,3-di- and 1,3,5-trichlorides. J. Org. Chem. 2000, 65, 2875–2879; (e) De Vicente , J. ; Arrayas , R. G. ; Carretero , J. C. An efficient and stereoselective synthesis of enantiopure 1,2,7-trihydroxylated pyrrolizidines. Tetrahedron Lett. 1999, 40, 6083–6086; (b) Paolucci , C. ; Venturelli , F. ; Fava , A. Chiral building blocks from 1,4:3,6-dianhydrohexitols, III: An expeditious enantiospecific synthesis of the Geissman–Waiss lactone. Tetrahedron Lett. 1995, 36, 8127–8129.
   Web of Science ®Google Scholar
• Tang , M. ; Pyne , S. G. Asymmetric synthesis of (−)-7-epiaustraline and (+)-1,7-diepiaustraline . J. Org. Chem. 2003 , 68 , 7818 – 7824 .
   PubMed Web of Science ®Google Scholar
• Romero , A. ; Wong , C. H. Chemo-enzymatic total synthesis of 3-epiaustraline, australine, and 7-epialexine . J. Org. Chem. 2000 , 65 , 8264 – 8268 .
   PubMed Web of Science ®Google Scholar
• Lalezari , I. ; Schwartz , E. L. Synthesis and antineoplastic activity of 5-aryl-2,3-dihydropyrrolo[2,1-b]thiazole-6,7-dimethanol 6,7-bis(isopropylcarbamates) . J. Med. Chem. 1988 , 31 , 1427 – 1429 .
   PubMed Web of Science ®Google Scholar
• Aicher , T. D. ; Balkan , B. ; Bell , P. A. ; Brand , L. J. ; Cheon , S. H. ; Deems , R. O. ; Fell , J. B. ; Fillers , W. S. ; Fraser , J. D. ; Gao , J. ; Knorr , D. C. ; Kahle , G. G. ; Leone , C. L. ; Nadelson , J. ; Simpson , R. ; Smith , H. C. Substituted tetrahydropyrrolo[2,1-b]oxazol-5(6H)-ones and tetrahydropyrrolo[2,1-b]thiazol-5(6H)-ones as hypoglycemic agents . J. Med. Chem. 1998 , 41 , 4556 – 4566 .
   PubMed Web of Science ®Google Scholar
• Tverdokhlebov , A. V. ; Resnyanska , E. V. ; Tolmachev , A. A. ; Andrushko , A. P. A novel approach to pyrrolo[2,1-b]thiazoles . Synthesis 2003 , 2632 .
   Web of Science ®Google Scholar
• (a) Baldwin , J. E. ; Lowe , C. ; Schofield , C. J. ; Lee , E. A γ-lactam analogue of penems possessing antibacterial activity . Tetrahedron Lett. 1986 , 27 , 3461 – 3464 ; (b) Boyd , D. B. ; Elzey , T. K. ; Hatfield , L. D. ; Kinnick , M. D. ; Morin Jr. , J. M. γ-Lactam analogues of the penems . Tetrahedron Lett. 1986 , 27 , 3453 – 3456
   Web of Science ®Google Scholar
• (a) Coldham , I. ; Hufton , R. Intramolecular dipolar cycloaddition reactions of azomethine ylides . Chem. Rev. 2005 , 105 , 2765 – 2810 ; (b) Pandey , G. ; Banerjee , P. ; Gadre , S. R. Construction of enantiopure pyrrolidine ring system via asymmetric [3 + 2]-cycloaddition of azomethine ylides . Chem. Rev. 2006 , 106 , 4484 – 4517 ; (c) Vedejs , E. ; Klapers , A. ; Naidu , B. N. ; Piotrowski , D. W. ; Tucci , F. C. Enantiocontrolled synthesis of (1S,2S)-6-desmethyl-(methylaziridino)mitosene . J. Am. Chem. Soc. 2000 , 122 , 5401 – 5404 .
   PubMed Web of Science ®Google Scholar
• Basaviah , D. ; Rao , A. J. ; Satyanarayana , T. Recent advances in the Baylis–Hillman reaction and applications . Chem. Rev. 2003 , 103 , 811 – 891 ; (b) Ciganek , E. In Organic Reactions; Wiley: New York, 1997; Vol. 51, p. 201–350 .
   PubMed Web of Science ®Google Scholar
• Coelho , F. ; Diaz , G. ; Abella , C. A. M. ; Almeida , W. P. The Baylis–Hillman reaction with chiral α-amino aldehydes under racemization-free conditions . Synlett. 2006 , 435 – 439 .
   Web of Science ®Google Scholar
• Roush , W. R. ; Brown , B. B. A highly diastereo- and enantioselective synthesis of the top half of kijanolide . J. Org. Chem. 1993 , 58 , 2151 – 2161 .
   Web of Science ®Google Scholar
• Jenn , T. ; Heissler , D. Synthesis of tricyclopolyprenols via a radical addition and a stereoselective elimination, part I: Methodology . Tetrahedron 1998 , 54 , 97 – 106 ; (b) Grassi , D. ; Lippuner , V. ; Aebi , M. ; Brunnerm , J. ; Vasella , A. Synthesis and enzymatic phosphorylation of a photoactivatable dolichol analogue . J. Am. Chem. Soc. 1997 , 119 , 10992 – 10999 .
   Web of Science ®Google Scholar
• (a) Mateus , C. R. ; Feltrin , M. P. ; Costa , A. M. ; Coelho , F. ; Almeida , W. P. Diastereoselectivity in heterogeneous catalytic hydrogenation of Baylis–Hillman adducts: Total synthesis of (±)-sitophilate . Tetrahedron 2001 , 57 , 6901 – 6908 ; (b) Basavaiah , D. ; Hyma , R. S. Synthetic applications of the baylis-hillman reaction: Simple synthesis of [2E]-2-butyloct-2-enal and [2E]-2-tridecylheptadec-2-enal . Tetrahedron 1996 , 52 , 1253 – 1258 .
   Web of Science ®Google Scholar
• (a) Kathiravan , S. ; Raghunathan , R. Synthesis of macrocyclic bis-imidazolidine derivatives through [3 + 2]cycloaddition reaction. Synlett. 2009, 1126–1129; (b) Suresh Babu , A. R. ; Raghunathan , R. ; Satiskumar , B. K. A facile synthesis of ferrocene grafted N-methyl-spiropyrrolidines through 1,3-dipolar cycloaddition of azomethine ylides. Tetrahedron Lett. 2009, 50, 2818–2821; (c) Poornachandran , M. ; Raghunathan , R. Tetrahedron 2008, 64, 6461–6474; (d) Poornachandran , M. ; Raghunathan , R. Tetrahedron: Asymmetry 2008, 19, 2177–2183.
   Google Scholar
• Selvanayagam , S. ; Sridhar , B. ; Ravikumar , K. ; Kathiravan , S. ; Raghunathan , R. Methyl-6,6a,7,7a8,9,10,11a-octahydro-7-(2-chlorophenyl)naphtho[2,1-b]pyrano thiapyrrolizine-6a-carboxylate . Acta Cryst. 2010 , E66 , o2098 .
   Google Scholar