SCOPUS 정보 검색 플랫폼

Volumn 10, Issue 4, 2012, Pages 825-834

A formal [3+3]-annulation-based approach to pancratistatins: Total synthesis of (±)-7-deoxy-pancratistatin and its 2-epi and 2,4-diepi analogues

(5) Nieto García, Olaia a Lago Santomé, Hugo a Cagide Fagín, Fernando b Ortiz Lara, Juan Carlos c Alonso, Ricardo a

a UNIVERSITY OF SANTIAGO DE COMPOSTELA (Spain)

b UNIVERSITY OF PORTO (Portugal)

c Sintenovo SA de CV: Calle 4 ^* (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOTOXIC ACTIVITIES; HUMAN LUNG; TOTAL SYNTHESIS; TUMORAL CELLS;

CELL CULTURE;

CYTOTOXICITY;

7 DEOXYPANCRATISTATIN; 7-DEOXYPANCRATISTATIN; AMARYLLIDACEAE ALKALOID; ANTINEOPLASTIC AGENT; ISOQUINOLINE DERIVATIVE;

ARTICLE; CHEMISTRY; HUMAN; LILIACEAE; LUNG TUMOR; SYNTHESIS; TUMOR CELL LINE;

AMARYLLIDACEAE ALKALOIDS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CELL LINE, TUMOR; HUMANS; ISOQUINOLINES; LILIACEAE; LUNG NEOPLASMS;

EID: 84555178958 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/c1ob06374j Document Type: Article

Times cited : (17)

References (26)

1
- 70350085648
- L. Ingrassia F. Lefranc V. Mathieu F. Darro R. Kiss Translational Oncology 2008 1 1 13
- (2008) Translational Oncology , vol.1 , pp. 1-13
- Ingrassia, L.¹ Lefranc, F.² Mathieu, V.³ Darro, F.⁴ Kiss, R.⁵

2
- 47249124531
- See also the "Introduction" section of
- A. Kornienko A. Evidente Chem. Rev. 2008 108 1982 2014
- (2008) Chem. Rev. , vol.108 , pp. 1982-2014
- Kornienko, A.¹ Evidente, A.²

3
- 77951783308
- references cited therein For an account covering the progress in the synthesis of Amaryllidaceae constituents and some truncated derivatives from 1996 to the fall of 2004, with a detailed treatment of the total synthesis of pancratistatin, narciclasine, 7-deoxy-pancratistatin and lycoricidine, see
- J. Collins U. Rinner M. Moser T. Hudlicky I. Ghiviriga A. E. Romero A. Kornienko D. Ma C. Griffin S. Pandey J. Org. Chem. 2010 75 3069 3084
- (2010) J. Org. Chem. , vol.75 , pp. 3069-3084
- Collins, J.¹ Rinner, U.² Moser, M.³ Hudlicky, T.⁴ Ghiviriga, I.⁵ Romero, A.E.⁶ Kornienko, A.⁷ Ma, D.⁸ Griffin, C.⁹ Pandey, S.¹⁰

4
- 14644422595
- For studies on the anticancer activity and the pharmaceutical potential of pancratistatin, see
- U. Rinner T. Hudlicky Synlett 2005 365 387
- (2005) Synlett , pp. 365-387
- Rinner, U.¹ Hudlicky, T.²

5
- 78751503441
- C. Griffin C. Hamm J. McNulty S. Pandey Cancer Cell Int. 2010 10 6
- (2010) Cancer Cell Int. , vol.10 , pp. 6
- Griffin, C.¹ Hamm, C.² McNulty, J.³ Pandey, S.⁴

6
- 78751518833
- references therein. See also the "Introduction and Biomedical Significance" and the "Conclusion" sections of reference 5a, and the "Introduction" section of reference 5b For a review on the total synthesis of pancratistatin including data on its isolation from natural sources and biomedical significance, see
- C. Griffin A. Karnik J. McNulty S. Pandey Mol. Cancer Ther. 2011 10 57 68
- (2011) Mol. Cancer Ther. , vol.10 , pp. 57-68
- Griffin, C.¹ Karnik, A.² McNulty, J.³ Pandey, S.⁴

7
- 56749102375
- For the last total synthesis reported to date and not included in ref. 4a, see
- M. Manpadi A. Kornienko Org. Prep. Proced. Int. 2008 40 107 161
- (2008) Org. Prep. Proced. Int. , vol.40 , pp. 107-161
- Manpadi, M.¹ Kornienko, A.²

8
- 84889706894
- D. Johan Hygum M. Robert Eur. J. Org. Chem. 2009 4666 4673
- (2009) Eur. J. Org. Chem. , pp. 4666-4673
- Johan Hygum, D.¹ Robert, M.²

9
- 33749672581
- J. C. Ortiz L. Ozores F. Cagide-Fagin R. Alonso Chem. Commun. 2006 4239 4241
- (2006) Chem. Commun. , pp. 4239-4241
- Ortiz, J.C.¹ Ozores, L.² Cagide-Fagin, F.³ Alonso, R.⁴

10
- 37049067873
- M. G. Banwell B. D. Bissett S. Busato C. J. Cowden G. C. R. Hockless J. W. Holman R. W. Read A. W. Wu J. Chem. Soc., Chem. Commun. 1995 2551 2553
- (1995) J. Chem. Soc., Chem. Commun. , pp. 2551-2553
- Banwell, M.G.¹ Bissett, B.D.² Busato, S.³ Cowden, C.J.⁴ Hockless, G.C.R.⁵ Holman, J.W.⁶ Read, R.W.⁷ Wu, A.W.⁸

11
- 0004992299
- Several examples can be found in the account of Hudlicky and Rinner: reference 4b. For a recent application, see
- M. G. Banwell C. J. Cowden R. W. Gable J. Chem. Soc., Perkin Trans. 1 1994 3515 3518
- (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 3515-3518
- Banwell, M.G.¹ Cowden, C.J.² Gable, R.W.³

12
- 79955437710
- S. L. Poe J. P. Morken Angew. Chem., Int. Ed. 2011 50 4189 4192
- (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 4189-4192
- Poe, S.L.¹ Morken, J.P.²

13
- 43449108880
- A detailed preparation procedure and full characterization data for 12a can be found in reference 6 (in its reference 16) See
- P. Martínez-Bescos F. Cagide-Fagín L. F. Roa J. C. Ortiz-Lara K. Kierus L. Ozores-Viturro M. Fernández-González R. Alonso J. Org. Chem. 2008 73 3745 3753
- (2008) J. Org. Chem. , vol.73 , pp. 3745-3753
- Martínez-Bescos, P.¹ Cagide-Fagín, F.² Roa, L.F.³ Ortiz-Lara, J.C.⁴ Kierus, K.⁵ Ozores-Viturro, L.⁶ Fernández-González, M.⁷ Alonso, R.⁸

14
- 0000908289
- J. O. Osby B. Ganem Tetrahedron Lett. 1985 26 6413 6416
- (1985) Tetrahedron Lett. , vol.26 , pp. 6413-6416
- Osby, J.O.¹ Ganem, B.²

15
- 44649091928
- references cited therein In our hands, β-furyl-α-nitro- α,β-enals (e.g., the precursor of 18) showed to be both more stable and convenient to prepare than the corresponding β-aryl-α-nitro- α,β-enals (e.g., 10a, the precursor of 12a): see reference 9 A multigram-scale detailed preparation of 18 from furfural, including a timetable, is described in the experimental section and the supporting information of
- H. Krawczyk L. Albrecht J. Wojciechowski W. M. Wolf U. Krajewska M. Rózalski Tetrahedron 2008 64 6307 6314
- (2008) Tetrahedron , vol.64 , pp. 6307-6314
- Krawczyk, H.¹ Albrecht, L.² Wojciechowski, J.³ Wolf, W.M.⁴ Krajewska, U.⁵ Rózalski, M.⁶

16
- 78650167368
- F. Cagide-Fagin R. Alonso Eur. J. Org. Chem. 2010 35 6741 6747
- (2010) Eur. J. Org. Chem. , vol.35 , pp. 6741-6747
- Cagide-Fagin, F.¹ Alonso, R.²

17
- 33646941664
- J. Cossy D. Belotti Tetrahedron 2006 62 6459 6470
- (2006) Tetrahedron , vol.62 , pp. 6459-6470
- Cossy, J.¹ Belotti, D.²

18
- 33847029949
- For an X-ray structure and a cif file, see the ESI For a review on acyloxyborohydrides, see
- M. Inui A. Nakazaki S. Kobayashi Org. Lett. 2007 9 469 472
- (2007) Org. Lett. , vol.9 , pp. 469-472
- Inui, M.¹ Nakazaki, A.² Kobayashi, S.³

19
- 0032328845
- For examples, see
- G. W. Gribble Chem. Soc. Rev. 1998 27 395 404
- (1998) Chem. Soc. Rev. , vol.27 , pp. 395-404
- Gribble, G.W.¹

20
- 0020673714
- A. K. Saksena P. Mangiaracina Tetrahedron Lett. 1983 24 273 276
- (1983) Tetrahedron Lett. , vol.24 , pp. 273-276
- Saksena, A.K.¹ Mangiaracina, P.²

21
- 0021678065
- M. D. Turnbull G. Hatter D. E. Ledgerwood Tetrahedron Lett. 1984 25 5449 5452
- (1984) Tetrahedron Lett. , vol.25 , pp. 5449-5452
- Turnbull, M.D.¹ Hatter, G.² Ledgerwood, D.E.³

22
- 3142712837
- Y.-T. Liu J. K. Wong M. Tao R. Osterman M. Sannigrahi V. M. Girijavallabhan A. Saksena Tetrahedron Lett. 2004 45 6097 6100
- (2004) Tetrahedron Lett. , vol.45 , pp. 6097-6100
- Liu, Y.-T.¹ Wong, J.K.² Tao, M.³ Osterman, R.⁴ Sannigrahi, M.⁵ Girijavallabhan, V.M.⁶ Saksena, A.⁷

23
- 0037073868
- Natural narciclasine was kindly supplied by Dr A. Jiménez, of CBM-CSIC (Madrid, Spain)
- T. Hudlicky U. Rinner D. Gonzalez H. Akgun S. Schilling P. Siengalewicz T. A. Martinot G. R. Pettit J. Org. Chem. 2002 67 8726 8743
- (2002) J. Org. Chem. , vol.67 , pp. 8726-8743
- Hudlicky, T.¹ Rinner, U.² Gonzalez, D.³ Akgun, H.⁴ Schilling, S.⁵ Siengalewicz, P.⁶ Martinot, T.A.⁷ Pettit, G.R.⁸

24
- 0036148244
- G. R. Pettit N. Melody D. L. Herald J. M. Schmidt R. K. Pettit J. C. Chapuis Heterocycles 2002 56 139 155
- (2002) Heterocycles , vol.56 , pp. 139-155
- Pettit, G.R.¹ Melody, N.² Herald, D.L.³ Schmidt, J.M.⁴ Pettit, R.K.⁵ Chapuis, J.C.⁶

25
- 32644435896
- G. R. Pettit S. A. Eastham N. Melody B. Orr D. L. Herald J. McGregor J. C. Knight D. L. Doubek G. R. Pettit L. C. Garner J. A. Bell J. Nat. Prod. 2006 69 7 13
- (2006) J. Nat. Prod. , vol.69 , pp. 7-13
- Pettit, G.R.¹ Eastham, S.A.² Melody, N.³ Orr, B.⁴ Herald, D.L.⁵ McGregor, J.⁶ Knight, J.C.⁷ Doubek, D.L.⁸ Pettit, G.R.⁹ Garner, L.C.¹⁰ Bell, J.A.¹¹

26
- 2342653649
- aq
- U. Rinner H. L. Hillebrenner D. R. Adams T. Hudlicky G. R. Pettit Bioorg. Med. Chem. Lett. 2004 14 2911 2915
- (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 2911-2915
- Rinner, U.¹ Hillebrenner, H.L.² Adams, D.R.³ Hudlicky, T.⁴ Pettit, G.R.⁵

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.