Synthetic studies on lytophilippine A: Synthesis of the proposed structure

Organic Letters

Volumn 13, Issue 9, 2011, Pages 2476-2479

  Jang, Ki Po ^a   Choi, Soo Young ^a   Chung, Young Keun ^a   Lee, Eun ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

LYTOPHILIPPINE A; MACROLIDE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS;

CYCLIZATION; MACROLIDES; MOLECULAR STRUCTURE;

EID: 79955606252     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2007296     Document Type: Article

References (20)

1. R̂ezanka, T.; Hanuŝ, L. O.; Dembitsky, V. M. Tetrahedron 2004, 60, 12191-12199
2. Gille, A.; Hiersemann, M. Org. Lett. 2010, 12, 5258-5261
3. Jung, J. H.; Kim, Y. W.; Kim, M. A.; Choi, S. Y.; Chung, Y. K.; Kim, T.-R.; Shin, S.; Lee, E. Org. Lett. 2007, 9, 3225-3228
4. Moon, H. R.; Choi, W. J.; Kim, H. O.; Jeong, L. S. Tetrahedron: Asymmetry 2002, 13, 1189-1193
5. A higher concentration of methanol probably prevented a retro-Michael reaction, and a higher yield of 8 was obtained.
6. Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889-3890
7. Ostermeier, M.; Brunner, B.; Korff, C.; Helmchen, G. Eur. J. Org. Chem. 2003, 3453-3459
8. Fuürstner, A.; Bouchez, L. C.; Funel, J.-A.; Liepins, V.; Porée, F.-H.; Gilmour, R.; Beaufils, F.; Laurich, D.; Tamiya, M. Angew. Chem., Int. Ed. 2007, 46, 9265-9270
9. Betche, H.-J.; Irdam, E. A.; Padilla, A. G.; Pearlman, B.; Perrault, W. R.; Vanalsten, J.; Franczyk, T. S. WO 2007/010387 A2.
10. Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127-2129
11. Cho, B. H.; Kim, J. H.; Jeon, H. B.; Kim, K. S. Tetrahedron 2005, 61, 4341-4346
12. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936-3938
13. Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterma, R. L. J. Am. Chem. Soc. 1990, 112, 6339-6348
14. Kalesse, M.; Chary, K. P.; Quitschalle, M.; Burzlaff, A.; Kasper, C.; Scheper, T. Chem.-Eur. J. 2003, 9, 1129-1136
15. Mitsunobu, O.; Yamada, Y. Bull. Chem. Soc. Jpn. 1967, 40, 2380-2382
16. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956
17. The structure of 35 was confirmed by X-ray diffraction studies. CCDC 812839 contains the supplementary crystallographic data for this compound. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
18. From previous studies, (3) it is known that the present sequence is more efficient overall than the direct use of (Z)-(S)-β-alkoxyvinyl sulfoxide.
19. See the Supporting Information for the stereochemical assignment through the corresponding carbonates.
20. 2O, and none matched the reported data. We did not yet find any crystalline derivative of 1.