On the use of the modified Julia olefination for bryostatin synthesis

Tetrahedron Letters

Volumn 49, Issue 44, 2008, Pages 6352-6355

  Allen, Joanne V ^a   Green, Anthony P ^b   Hardy, Simon ^b   Heron, Nicola M ^a   Lee, Alan T L ^b   Thomas, Eric J ^b  

^a ASTRAZENECA   (United Kingdom)

^b UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKENE; BENZOTHIAZOLE DERIVATIVE; BRYOSTATIN;

ARTICLE; DRUG HYDROXYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; MODIFIED JULIA OLEFINATION; OLEFINATION; PROTON TRANSPORT;

EID: 51749093314     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.08.075     Document Type: Article

References (28)

1. Hale K.J., Hummersone M.G., Manaviazar S., and Frigerio M. Nat. Prod. Reports 19 (2002) 413
2. Masamune S. Pure Appl. Chem. 60 (1988) 1587
3. Kageyama M., Tamura T., Nantz M.H., Roberts J.C., Somfrai P., Whitenour D.C., and Masamune S. J. Am. Chem. Soc. 112 (1990) 7407
4. Evans D.A., Carter P.H., Carreira E.M., Prunet J.A., Charette A.B., and Lautens M. Angew. Chem., Int. Ed. 37 (1998) 2354
5. Evans D.A., Carter P.H., Carreira E.M., Prunet J.A., Charette A.B., and Lautens M. J. Am. Chem. Soc. 121 (1999) 7540
6. Ohmori K., Ogawa Y., Obitsu T., Ishikawa Y., Nishiyama S., and Yamamura S. Angew. Chem., Int. Ed. 39 (2000) 2290
7. Manaviazar S., Frigerio M., Bhatia G.S., Hummerstone M.G., Aliev A.E., and Hale K. Org. Lett. 8 (2006) 4477
8. Wender P.A., Baryza J.L., Bennett C.E., Bi F.C., Brenner S.E., Clarke M.O., Horan J.C., Kan C., Lacote E., Lippa B., Nell P., and Turner T.M. J. Am. Chem. Soc. 124 (2002) 13648
9. Wender P.A., DeChristopher B.A., and Schrier A.J. J. Am. Chem. Soc. 130 (2008) 6658
10. Wender P.A., Horan J.C., and Verma V.A. Org. Lett. 8 (2006) 5299
11. Wender P.A., and Horan J.C. Org. Lett. 8 (2006) 4581
12. Ball M., Bradshaw B.J., Dumeunier R., Gregson T.J., MacCormick S., Omori H., and Thomas E.J. Tetrahedron Lett. 47 (2006) 2223
13. Trost B.M., Yang H., Thiel O.R., Frontier A.J., and Brindle C.S. J. Am. Chem. Soc. 129 (2007) 2206
14. O'Brien M., Taylor N.H., and Thomas E.J. Tetrahedron Lett. 43 (2002) 5491
15. Aldehyde 8 was prepared from ester 17:. Ball M., Baron A., Bradshaw B., Omori H., MacCormick S., and Thomas E.J. Tetrahedron Lett. 45 (2004) 8737
16. Sulfone 7 was prepared from 2,2-dimethyl-3-phenylthio-propan-1-ol by conversion to its O-p-methoxybenzyl ether followed by S-oxidation using Oxone.
17. Blakemore P.R. J. Chem. Soc., Perkin Trans. 1 (2002) 2563
18. Baudin J.B., Horeau G., Julia S.A., and Ruel O. Tetrahedron Lett. 32 (1991) 1175
19. Sulfone 9 was prepared from alcohol 11 by a Mitsunobu displacement using 2-mercaptobenzothiazole followed by oxidation.
20. This approach has recently been applied to the synthesis of the C(17)-C(27) fragment of bryostatin 1; Green, A. P.; Hardy, S.; Thomas, E. J. Synlett 2008, 2103.
21. Trieselmann T., Hoffmann R.W., and Menzel K. Eur. J. Org. Chem. 7 (2002) 1292
22. Rondestvedt C. J. Org. Chem. 26 (1961) 2247
23. Zhang Y., and Sammakia T. J. Org. Chem. 71 (2006) 6262
24. Ferezou J.P., and Julia M. Tetrahedron 46 (1990) 475
25. Sugiyama H., Yokokawa F., and Shiori T. Tetrahedron 59 (2003) 6579
26. Soll R.M., and Setz S.P. Tetrahedron Lett. 28 (1987) 5457
27. Armstrong A., Barsonti P.A., Blench T.J., and Ogilvie R. Tetrahedron 59 (2003) 367
28. Armstrong A., Barsanti P.A., Jones L.H., and Ahmed G. J. Org. Chem. 65 (2000) 7020