Ketal-tethered ring-closing metathesis. An unconventional approach to constructing spiroketals and total synthesis of an insect pheromone

Tetrahedron Letters

Volumn 45, Issue 28, 2004, Pages 5505-5510

  Ghosh, Sunil K ^a   Hsung, Richard P ^a   Wang, Jiashi ^a  

^a University of Minnesota   (United States)

Author keywords

Insect hormone; Ketal tethered reactions; RCM; Spiroketals

Indexed keywords

ACETAL; INSECT HORMONE; PHEROMONE;

ARTICLE; RING CLOSING METATHESIS; STEREOCHEMISTRY;

INSECTA;

EID: 2942665448     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.05.017     Document Type: Article

References (42)

1. For recent reviews on metathesis, see: Grubbs R.H., Miller S.J., Fu G.C. Acc. Chem. Res. 28:1995;446
2. Schrock R.R. Tetrahedron. 55:1999;8141
3. Fürstner A. Angew. Chem., Int. Ed. 39:2000;3012
4. Trnka T.M., Grubbs R.H. Acc. Chem. Res. 34:2001;18
5. Hoveyda A.H., Schrock R.R. Chem. Eur. J. 7:2001;945
6. For reviews on enyne RCM, see: Mori M. Fürstner A. Topics in Organometallic Chemistry. Vol. 1:1998;133 Springer, Berlin, Heidelberg
7. Mori M. J. Synth. Org. Chem. Jpn. 56:1998;115
8. Keller V.A., Martinellie J.R., Strieter E.R., Burke S.D. Org. Lett. 4:2002;467
9. Voight E.A., Rein C., Burke S.D. J. Org. Chem. 67:2002;8489
10. Burke S.D., Voight E.A. Org. Lett. 3:2001;237
11. Burke S.D., Muller N., Beaudry C.M. Org. Lett. 1:1999;1827
12. Scholl M., Grubbs R.H. Tetrahedron Lett. 40:1999;1425
13. Kinderman S.S., Doodeman R., van Beijma J.W., Russcher J.C., Tjen K.C.M.F., Kooistra T.M., Mohaselzadeh H., van Maarseveen J.H., Hiemstra H., Schoemaker H.E., Rutjes F.P.J.T. Adv. Syn. Catal. 344:2002;736
14. van Hooft P.A.V., Leeuwenburgh M.A., Overkleeft H.A., van der Marel G.A., van Boeckel C.A.A., van Boom J.H. Tetrahedron Lett. 39:1998;6061
15. Bassindale M.J., Hamley P., Leitner A., Harrity J.P.A. Tetrahedron Lett. 40:1999;3247
16. For a review on chemistry of spiroketals, see: Perron F., Albizati K.F. Chem. Rev. 89:1989;1617
17. 2 (100 mL) at rt was added pyridinium p-toluenesulfonate (187.0 mg, 0.074 mmol, 10 mol %). The reaction mixture was stirred at rt for 12 h. The solvent was removed in vacuo and the crude product was purified using silica gel flash column chromatography (gradient eluent: 5-10% EtOAc in hexanes) to afford cyclic ketals 10a and 10s (combined mass and yield: 1.29 g, 72%) with a 1.6:1 diastereomeric ratio for 10a:10s. Isomers 10a and 10s can be cleanly separated via a second and more careful flash column chromatography.
18. The X-ray structure of 13a is available upon request
19. For a reference see: Schwab P., France M.B., Ziller J.W., Grubbs R.H. Angew. Chem., Int. Ed. Engl. 34:1995;2039
20. For some earlier work, see: Weskamp T., Schattenmann W.C., Spiegler M., Herrmann W.A. Angew. Chem., Int. Ed. 37:1998;2490
21. Herrmann W.A., Köcher C. Angew. Chem., Int. Ed. 36:1997;2162
22. Huang J., Stevens E.D., Nolan S.P., Petersen J.L. J. Am. Chem. Soc. 121:1999;2674. and references cited therein
23. Huang J., Schanz H.-J., Stevens E.D., Nolan S.P. Organometallics. 18:1999;2370
24. Scholl M., Ding S., Lee C.W., Grubbs R.H. Org. Lett. 1:1999;953
25. Tengoe J., Bergstroem G., Borg-Karlson A.K., Groth I., Francke W. Z. Naturforsch., C: Biosci. 37:1982;376
26. Bergstroem G., Tengoe J., Reith W., Francke W. Z. Naturforsch., C: Biosci. 37:1982;1124
27. Francke W., Reith W., Bergstroem G., Tengoe J. Z. Naturforsch., C: Biosci. 36:1981;928
28. Francke W., Reith W., Bergstroem G., Tengoe J. Naturwissenschafter. 67:1980;149
29. Isaksson R., Liljefors L., Reinholdsson P. J. Chem. Soc., Chem. Commun. 1984;137
30. Boeckman R.K. Jr., Bruza K.J. Tetrahedron. 37:1981;3997
31. Postema M.H.D. Tetrahedron. 48:1992;8545
32. Postema M.H.D. C-Glycoside Synthesis. 1995;CRC, Ann Arbor
33. Levy D.E., Tang C. The Chemistry of C-Glycosides, 1st ed. Vol. 13:1995;Pergamon
34. Parker K.A. Pure Appl. Chem. 66:1994;2135
35. Larsen C.H., Ridgeway B.H., Shaw J.T., Woerpel K.A. J. Am. Chem. Soc. 121:1999;12208
36. Shaw J.T., Woerpel K.A. J. Org. Chem. 62:1997;6706
37. Romero J.A.C., Tabacco S.A., Woerpel K.A. J. Am. Chem. Soc. 122:2000;168
38. Matsutani H., Ichikawa S., Yaruva J., Kusumoto T., Hiyama T. J. Am. Chem. Soc. 119:1997;4541
39. Woods R.J., Andrews C.W., Bowen J.P. J. Am. Chem. Soc. 114:1992;859
40. Miljkovic M., Yeagley D., Deslongchamps P., Dory Y.L. J. Org. Chem. 62:1997;7597
41. Ballini R., Bosica G., Schaafstra R. Liebig Ann. Chem. 1994;1235
42. Weber G.F., Hall S.S. J. Org. Chem. 44:1979;364