Synthesis of (±)-diospongin a: A hetero-diels-alder and c-glycosylation approach

Synthesis

Volumn , Issue 14, 2010, Pages 2419-2423

  More, Jesse D ^a  

^a LOYOLA UNIVERSITY MARYLAND   (United States)

Author keywords

Diels Alder reaction; glycosylation; natural products; neighboring group effects

Indexed keywords

DIELS-ALDER REACTION; HETERO-DIELS-ALDER; HETERO-DIELS-ALDER REACTIONS; NATURAL PRODUCTS; NEIGHBORING-GROUP EFFECTS; STEREO-SELECTIVE;

ESTERIFICATION; GLYCOSYLATION; SYNTHESIS (CHEMICAL);

STEREOSELECTIVITY;

2 ACETOXY 6 PHENYLTETRAHYDRO 2H PYRAN 4 YL BENZOATE; 2 PHENYL 2H PYRAN 4(3H) ONE; 2 PHENYL 3,4 DIHYDRO 2H PYRAN 4 OL; 4 (TERT BUTYLDIMETHYLSILYLOXY) 6 PHENYLTETRAHYDRO 2H PYRAN 2 YL ACETATE; 4 HYDROXY 6 PHENYLTETRAHYDRO 2H PYRAN 2 YL ACETATE; DIOSPONGIN A; DIOSPONGIN B; TERT BUTYLDIMETHYL 2 PHENYL 3,4 DIHYDRO 2H PYRAN 4 YLOXY SILANE; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROSPRAY; GLYCOSYLATION; HYDROGENATION; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; THIN LAYER CHROMATOGRAPHY;

EID: 77954583308     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218784     Document Type: Article

References (32)

1. Yin J, Kouda K, Tezuka Y, Tran Q.-L, Miyahara T, Chen Y, Kadota S, Planta Med. 2004 70 54
2. Bressy B, Allais F, Cossy J, Synlett 2006 3455
3. Bates R W., Song P, Tetrahedron 2007 63 4497
4. Sabitha G, Padmaja P, Yadav J S., Helv. Chim. Acta 2008 91 2235
5. Yadav J S., Padmavani B, Reddy B V. S., Venugopal Ch, Rao A B., Synlett 2007 2045
6. Hiebel M.-A, Pelotier B, Piva O, Tetrahedron 2007 63 7874
7. Lee K, Kim H, Hong J, Org. Lett. 2009 11 5202
8. Kawai N, Hande S M., Uenishi J, Tetrahedron 2007 63 9049
9. Wang H, Shuhler B J., Xian M, Synlett 2008 2651
10. Sawant K B., Jennings M P., J. Org. Chem. 2006 71 7911
11. While this manuscript was in preparation, a hetero-Diels-Alder approach to the diospongins was reported, see:, Kumaraswamy G, Ramakrishna G, Naresh P, Jagadeesh B, Sridhar B, J. Org. Chem. 2009 74 8468
12. For general reviews of neighboring-group participation in glycosylation, see:, Demchenko A, In Handbook of Chemical Glycosylation Demchenko A Wiley-VCH Weinheim 2008 5-6
13. Hunig S, Angew. Chem., Int. Ed. Engl. 1964 3 548
14. Danishefsky S, Kerwin J F., Kobayashi S, J. Am. Chem. Soc. 1982 104 358
15. For a review, see:, Pellissier H, Tetrahedron 2009 65 2839
16. Ayala L, Lucero C G., Romero J A. C., Tabacco S A., Woerpel K A., J. Am. Chem. Soc. 2003 125 15521
17. For examples of 1,3-stereocontrol in O-glycosylation via anchimeric assistance, see Wiesner K, Tsai T Y. R., Jin H, Helv. Chim. Acta 1985 68 300
18. Binkley R W., Koholic D J., J. Carbohydr. Chem. 1988 7 487
19. Tanaka H, Yoshizawa A, Takahashi T, Angew. Chem. Int. Ed. 2007 46 2505
20. Hou D, Lowary T L., Carbohydr. Res. 2009 344 1911
21. Marzabadi C, Franck R W., Tetrahedron 2000 56 8385
22. Joly G D., Jacobsen E N., Org. Lett. 2002 4 1795
23. Joly G D., Ph.D. Thesis Harvard University Cambridge USA 2004
24. Moilanen S B., Tan D S., Org. Biomol. Chem. 2005 3 798
25. Kaneno D, Tomoda S, Tetrahedron Lett. 2009 50 329
26. For a review, see:, Corey E J., Helal C J., Angew. Chem. Int. Ed. 1998 37 1986
27. Gemal A L., Luche J L., J. Am. Chem. Soc. 1981 103 5454
28. Berkowitz D B., Danishefsky S J., Schulte G K., J. Am. Chem. Soc. 1992 114 4518
29. Mitsunobu O, Synthesis 1980 1
30. For a review, see:, Ferrier R J., Top. Curr. Chem. 2001 215 153
31. Bolitt V, Mioskowski C, Lee S.-G, Falck J R., J. Org. Chem. 1990 55 5812
32. N2 displacement of an equatorial leaving group. In the case of 11, a ring-flip to give an axial leaving group would force the phenyl group into a disfavored axial position. See:, Eliel E L., Wilen S H., Mander L N., In Stereochemistry of Organic Compounds John Wiley and Sons New York 1994 723