Synthesis of Novel laurenditerpenol analogues and their evaluation as HIF-1 activation inhibitors

Letters in Organic Chemistry

Volumn 6, Issue 4, 2009, Pages 269-271

  Athinaios, Nikolaos ^a   Kazantzis, Athanasios ^a   Putzker, Kerstin ^b   Lewis, Joe ^b   Pitsinos, Emmanuel N ^a  

^a Institute of Physical Chemistry   (Greece)

^b EMBL Heidelberg   (Germany)

Author keywords

Diels Alder reaction; Furan; Natural products; Olefin cross metathesis

Indexed keywords

EID: 69549110210     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017809788489891     Document Type: Article

References (21)

1. Melillo, G. Cancer Metastasis Rev., 2007, 26, 341.
2. Belozerov, V.E.; Van Meir, E.G. Anti-Cancer Drugs, 2005, 16, 901;
3. Park, J.-W.; Kim, M.-S. J. Pharmacol. Sci., 2004, 94, 221.
4. Mohammed, K.A.; Hossain, C.F.; Zhang, L.; Bruick, R.K.; Zhou, Y.-D.; Nagle, D.G. J. Nat. Prod., 2004, 67, 2002;
5. While this work was in progress, a total synthesis of laurenditerpenol established its absolute stereo structure as 1S-, 6R-, 7S-, 10R-, 11R-, 14S-, 15R-: Chittiboyina, A.G.; Kumar, G.M.; Carvalho, P.B.; Liu, Y.; Zhou, Y.-D.; Nagle, D.G.; Avery, M.A. J. Med. Chem., 2007, 50, 6299.
6. Recently a racemic total synthesis has been reported: Jung, M.E.; Im, G-Y.J. Tetrahedron Lett., 2008, 49, 4962.
7. Chatterjee, A.K.; Choi, T.L.; Sanders, D.P.; Grubbs, R.H. J. Am. Chem. Soc., 2003, 125, 11360;
8. Blechert, S.; Connon, S.J. Angew. Chem. Int. Ed., 2003, 42, 1900.
9. For enantioselective Diels-Alder reactions of dimethylfuran see: Liu, D.; Canales, E.; Corey, E.J. J. Am. Chem. Soc., 2007, 129, 1498.
10. Guth, H. Helv. Chim. Acta, 1996, 79, 15559;
11. Bergner, E.J.;Helmchen, G. Eur. J. Org. Chem., 2000, 419;
12. Chavan, S.P.; Kharul, R.K.; Sharma, A.K.; Chavan, S.P. Tetrahedron: Asymmetry, 2001, 12, 2985;
13. Serra, S.; Fuganti, C. Helv. Chim. Acta, 2004, 87, 2100.
14. Hayashi, Y.; Nakamura, M.; Nakao, S.; Inoue, T.; Shoji, M. Angew. Chem. Int. Ed., 2002, 41, 4079.
15. In analogy to: Paquette, L.A.; Kravetz, T.M.; Charumilind, P. Tetrahedron, 1986, 42, 1789.
16. Pitsinos, E.N.; Wascholowski, V.; Karaliota, S.; Rigou, C.; Couladouros, E.A.; Giannis, A. ChembioChem, 2003, 4, 1223.
17. 2Na requires 297.18305.
18. 2Na requires 297.18305.
19. Wang, G.L.; Semenza, G.L. Blood, 1993, 82, 3610;
20. Salnikow, K.; Su, W.; Blagosklonny, M.V.; Costa, M. Cancer Res., 2000, 60, 3375.
21. 50 value using XLfit (IDBS). The reported values are the average of 3 replicates.