A desymmetrization approach toward highly oxygenated cis-decalins

Organic Letters

Volumn 11, Issue 13, 2009, Pages 2884-2886

  Gromov, Alexey ^a   Enev, Valentin ^a   Mulzer, Johann ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; BRANIMYCIN; DECALIN; MACROLIDE; NAPHTHALENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTI-BACTERIAL AGENTS; MACROLIDES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NAPHTHALENES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 67649494474     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900834c     Document Type: Article

References (20)

1. (a) Enev, V. S.; Drescher, M.; Mulzer, J. Org. Lett. 2008, 10, 413-416.
2. (b) Enev, V. S.; Drescher, M.; Mulzer, J. Tetrahedron 2007, 63, 5930-5939.
3. Marchart, S.; Mulzer, J.; Enev, V. S. Org. Lett. 2007, 9, 813-816.
4. Felzmann, W.; Arion, V. B.; Mieusset, J. L.; Mulzer, J. Org. Lett. 2006, 8, 3849-3851.
5. (e) Review: Mulzer, J.; Castagnolo, D.; Felzmann, W.; Marchart, S.; Pilger, C.; Enev, V. S. Chem. Eur. J. 2006, 12, 5992-6001,
6. (a) Isolation, and biological activity of branimycin : Speitling, M. Ph.D. Thesis, Universität Göttingen, 1998.
7. (b) Speitling, M.; Grün-Wollny, I.; Hannske, F. G.; Laatsch, H. IRSEER Naturstofftage der DECHEMA e.V. Irsee 2000, 2001, poster sessions 12 and 13.
8. For similar desymmetrizations, see: (a) Lautens, M.; Fillion, E. J. Org. Chem. 1996, 61, 7994-7995.
9. (b) Lautens, M.; Fillion, E. J. Org. Chem. 1998, 63, 647-656.
10. Webster, R.; Böing, C.; Lautens, M. J. Am. Chem. Soc. 2009, 131, 444-445.
11. For preliminary studies on the synthesis of 4, see: Gromov, A.; Enev, V.; Mulzer, J. Synth. Commun., in press.
12. For a discussion of this phenomenon, see comment 1 in the Supporting Information.
13. Arrayas, R. G.; Cabrera, S.; Carretero, J. C. Org. Lett. 2003, 5, 1333-1336.
14. For a reliable scalable procedure for preparation of PMBCl, see: Chaudhari, S. S.; Akamanchi, K. G. Synlett 1999, 11, 1763-1765.
15. Lautens, M.; Rovis, T. Tetrahedron 1998, 54, 1107-1116.
16. It has to be pointed out that skipped dienes 11 and 13 (not shown, see the Supporting Information) proved to be air sensitive to give dienyl hydroperoxides (for a discussion, see comment 2 in the Supporting Information).
17. Toluene as a solvent was essential for a high yield of the desired products. Performing the reaction in THF resulted in thformation of ca 50% of compound 3′.
18. equation presented This solvent effect might be attributed to the higher Lewis acidity of aluminum species in the non-coordinating toluene. An increase in Lewis acidity presumably favors coordination of Al with the oxa-bridge and therefore facilitates the C-O bond cleavage. For other examples of the influence of Lewis acids on oxa-bridge opening, see: Lautens, M.; Chiu, P.; Ma, S.; Rovis, T. J. Am. Chem. Soc. 1995, 117, 532-533.
19. Cf. also: Plata, D. J.; Kallmerten, J. J. Am. Chem. Soc. 1998, 110, 4041-4042.
20. Felzmann, W.; Castagnolo, D.; Rosenbeiger, D.; Mulzer, J. Org. Chem. 2007, 72, 2182-2186.