First enantioselective synthesis of methyl (+)-7-methoxyanodendroate, an antitubercular dihydrobenzofuran

Tetrahedron Letters

Volumn 52, Issue 51, 2011, Pages 6988-6990

  Aumann, Kylee M ^a   Hungerford, Natasha L ^a   Coster, Mark J ^a  

^a GRIFFITH UNIVERSITY   (Australia)

Author keywords

Claisen rearrangement; Cross metathesis; Methyl (+) 7 methoxyanodendroate; Natural product synthesis; Shi epoxidation

Indexed keywords

DIHYDROBENZOFURAN DERIVATIVE;

ARTICLE; CLAISEN REARRANGEMENT; ENANTIOSELECTIVITY;

EID: 81255172110     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.10.095     Document Type: Article

References (22)

1. H.-Y. Huang, T. Ishikawa, C.-F. Peng, I.-L. Tsai, and I.-S. Chen J. Nat. Prod. 71 2008 1146 1151
2. The synthesis of racemic 1 has been described, but no spectroscopic data was reported: H. Ishii, T. Ishikawa, I.-S. Chen, and S.-T. Lu Tetrahedron Lett. 23 1982 4345 4348
3. Y. Kawase, S. Yamaguchi, O. Inoue, M. Sannomiya, and K. Kawabe Chem. Lett. 1980 1581 1584
4. M. Uyanik, H. Okamoto, T. Yasui, and K. Ishihara Science 328 2010 1376 1379
5. J. Magolan, and M.J. Coster J. Org. Chem. 74 2009 5083 5086
6. H. Jiang, and Y. Hamada Org. Biomol. Chem. 7 2009 4173 4176
7. H. Jiang, T. Sugiyama, A. Hamajima, and Y. Hamada Adv. Synth. Catal. 353 2011 155 162
8. S.C. Pelly, S. Govender, M.A. Fernandes, H.-G. Schmalz, and C.B. de Koning J. Org. Chem. 72 2007 2857 2864
9. J. Fischer, G.P. Savage, and M.J. Coster Org. Lett. 13 2011 3376 3379
10. S.C. Wilson, P.W. Howard, S.M. Forrow, J.A. Hartley, L.J. Adams, T.C. Jenkins, L.R. Kelland, and D.E. Thurston J. Med. Chem. 42 1999 4028 4041
11. M. Scholl, S. Ding, C.W. Lee, and R.H. Grubbs Org. Lett. 1 1999 953 956
12. R.W. Murray, and M. Singh Org. Synth. Coll. vol. 9 1998 288 293 1997, 74, 91-96
13. C.C. Lindsey, C. Gómez-Diaz, J.M. Villalba, and T.R.R. Pettus Tetrahedron 58 2002 4559 4565
14. R. Curci, M. Fiorentino, L. Troisi, J.O. Edwards, and R.H. Pater J. Org. Chem. 45 1980 4758 4760
15. For reviews on the Shi epoxidation, see: M. Frohn, and Y. Shi Synthesis 2000 1979 2000
16. O.A. Wong, and Y. Shi Chem. Rev. 108 2008 3958
17. Z.-X. Wang, Y. Tu, M. Frohn, J.-R. Zhang, and Y. Shi J. Am. Chem. Soc. 119 1997 11224 11235
18. L. Shu, and Y. Shi Tetrahedron 57 2001 5213 5218
19. J. Chapelat, A. Buss, A. Chougnet, and W.-D. Woggon Org. Lett. 10 2008 5123 5126
20. X.-Y. Wu, X. She, and Y. Shi J. Am. Chem. Soc. 124 2002 8792 8793
21. B. Wang, X.-Y. Wu, O.A. Wong, B. Nettles, M.-X. Zhao, D. Chen, and Y. Shi J. Org. Chem. 74 2009 3986 3989
22. N. Nieto, P. Molas, J. Benet-Buchholz, and A. Vidal-Ferran J. Org. Chem. 70 2005 10143 10146