Total synthesis of pteridic acids A and B

Tetrahedron

Volumn 64, Issue 21, 2008, Pages 4768-4777

  Paterson, Ian ^a   Anderson, Edward A ^a   Findlay, Alison D ^a   Knappy, Christopher S ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Aldol reaction; Natural products; Plant growth promoter; Spiroacetal

Indexed keywords

ACETAL DERIVATIVE; BORON; GROWTH PROMOTOR; NATURAL PRODUCT; POLYKETIDE; PTERIDIC ACID A; PTERIDIC ACID B; PYRIDINE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; DESS MARTIN OXIDATION; DRUG STRUCTURE; DRUG SYNTHESIS; PLANT GROWTH; PRIORITY JOURNAL; SPIROACETALIZATION; STRUCTURE ANALYSIS;

EID: 42249106212     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.01.132     Document Type: Article

References (35)

1. Aho J.E., Pihko P.M., and Rissa T.K. Chem. Rev. 105 (2005) 4406
2. Paterson I., Chen D.Y.-K., Coster M.J., Acena J.L., Bach J., Gibson K.R., Keown L.E., Oballa R.M., Trieselmann T., Wallace D.J., Hodgson A., and Norcross R.D. Angew. Chem., Int. Ed. 40 (2001) 4055
3. Paterson I., Coster M.J., Chen D.Y.-K., Oballa R.M., Wallace D.J., and Norcross R.D. Org. Biomol. Chem. 3 (2005) 2399
4. Paterson I., Coster M., Chen D.Y.-K., Gibson K.R., and Wallace D.J. Org. Biomol. Chem. 3 (2005) 2410
5. Paterson I., Coster M.J., Chen D.Y.-K., Acena J.L., Bach J., Keown L., and Trieselmann T. Org. Biomol. Chem. 3 (2005) 2420
6. Paterson I., Chen D.Y.-K., Coster M.J., Acena J.L., Bach J., and Wallace D.J. Org. Biomol. Chem. 3 (2005) 2431
7. Paterson I., Chen D.Y.-K., and Franklin A.S. Org. Lett. 4 (2002) 391
8. Paterson I., Findlay A.D., and Anderson E.A. Angew. Chem., Int. Ed. 46 (2007) 6699
9. Paterson I., Anderson E.A., Dalby S.M., Lim J.H., Loiseleur O., Maltas P., and Moessner C. Pure Appl. Chem. 79 (2007) 667
10. Paterson I., Anderson E.A., Dalby S.M., Genovino J., Lim J.H., and Moessner C. Chem. Commun. (2007) 1852
11. Paterson I., Anderson E.A., Dalby S.M., Lim J.H., Maltas P., and Moessner C. Chem. Commun. (2006) 4186
12. Paterson I., Anderson E.A., Dalby S.M., and Loiseleur O. Org. Lett. 7 (2005) 4121
13. Paterson I., Anderson E.A., Dalby S.M., and Loiseleur O. Org. Lett. 7 (2005) 4125
14. Igarashi Y., Iida T., Yoshida R., and Furumi T. J. Antibiot. 55 (2002) 764
15. Nakahata T., and Kuwahara S. Chem. Commun. (2005) 1028
16. Nakahata T., Fujimura S., and Kuwahara S. Chem.-Eur. J. 12 (2006) 4584
17. Paterson I., and Channon J.A. Tetrahedron Lett. 33 (1992) 797
18. Paterson I., Goodman J.M., and Isaka M. Tetrahedron Lett. 30 (1989) 7121
19. Paterson I., and Arnott E.A. Tetrahedron Lett. 39 (1998) 7185
20. Paterson I., Florence G.J., Gerlach K., Scott J.P., and Sereinig N. J. Am. Chem. Soc. 123 (2001) 9535
21. 3N.
22. For a review on asymmetric aldol reactions using boron enolates, see:. Paterson I., and Cowden C.J. Org. React. 51 (1997) 1
23. For DFT calculations on related aldol transition states, see:. Paton R.S., and Goodman J.M. Org. Lett. 8 (2006) 4299
24. Roush W.R. J. Org. Chem. 56 (1991) 4151
25. Gennari C., Vieth S., Comotti A., Vulpetti A., Goodman J.M., and Paterson I. Tetrahedron 48 (1992) 4439
26. Evans D.A., Chapman K.T., and Carreira E.M. J. Am. Chem. Soc. 110 (1988) 3560
27. Dess D.B., and Martin J.C. J. Org. Chem. 48 (1983) 4155
28. Paterson I., Wallace D.J., and Cowden C.J. Synthesis (1998) 639
29. Paterson I., Wallace D.J., and Velázquez S.M. Tetrahedron Lett. 35 (1994) 9083
30. Paterson I., and Wallace D.J. Tetrahedron Lett. 35 (1994) 9087
31. The configuration was established by the advanced Mosher method, see:. Ohtani I., Kusumi Y., Kashman H., and Kakisawa H. J. Am. Chem. Soc. 113 (1991) 4092 A reduced level of diastereoselectivity (90:10 dr) is observed for propyl ketone 21 relative to the analogous aldol reactions of the corresponding ethyl ketone (≥97:3 dr)
32. Ramirez F., Desai N.B., and McKelvie N. J. Am. Chem. Soc. 84 (1962) 1745
33. Corey E.J., and Fuchs P.L. Tetrahedron Lett. 13 (1972) 3769
34. Uenishi J., Kawahama R., Yonemitsu O., and Tsuji R. J. Org. Chem. 61 (1996) 5716
35. Uenishi J., Kawahara R., and Yonemitsu O. J. Org. Chem. 63 (1998) 8965