Stereoselective synthesis of (+)-hyptolide

Tetrahedron Letters

Volumn 44, Issue 9, 2003, Pages 1737-1739

  Murga, Juan ^a   García Fortanet, Jorge ^a   Carda, Miguel ^a   Marco, J Alberto ^b  

^a UNIVERSITAT JAUME I   (Spain)

^b UNIVERSITY OF VALENCIA   (Spain)

Author keywords

(+) hyptolide; Asymmetric allylboration; Asymmetric ethynylation; Chiral pool; Ring closing metathesis

Indexed keywords

HYPTOLIDE; LACTONE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CHIRALITY; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0037463510     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00125-4     Document Type: Article

References (33)

1. Negishi E., Kotora M. Tetrahedron. 53:1997;6707-6738.
2. Collins I. J. Chem. Soc., Perkin Trans. 1. 1999;1377-1395.
3. Hoffmann H.M.R., Rabe J. Angew. Chem., Int. Ed. 24:1985;94-110.
4. Birch A.J., Butler D.N. J. Chem. Soc. 1964;4167-4168.
5. Achmad S.A., Høyer T., Kjær A., Makmur L., Norrestam R. Acta Chem. Scand. 41B:1987;599-609.
6. Pereda-Miranda R., Fragoso-Serrano M., Cerda-García-Rojas C.M. Tetrahedron. 57:2001;47-53.
7. Alemany A., Márquez C., Pascual C., Valverde S., Martínez-Ripoll M., Fayos J., Perales A. Tetrahedron Lett. 20:1979;3583-3586.
8. Coleman M.T.D., English R.B., Rivett D.E.A. Phytochemistry. 26:1987;1497-1499.
9. Pereda-Miranda R., Hernández L., Villavicencio M.J., Novelo M., Ibarra P., Chai H., Pezzuto J.M. J. Nat. Prod. 56:1993;583-593.
10. Lichtenthaler F., Lorenz K., Ma W. Tetrahedron Lett. 28:1987;47-50.
11. Lorenz K., Lichtenthaler F. Tetrahedron Lett. 28:1987;6437-6440.
12. Valverde S., Hernández A., Herrádon B., Rabanal R.M., Martín-Lomas M. Tetrahedron. 43:1987;3499-3504.
13. Falomir E., Murga J., Carda M., Marco J.A. Tetrahedron Lett. 44:2003;539-541.
14. Carda M., Rodríguez S., Segovia B., Marco J.A. J. Org. Chem. 67:2002;6560-6563.
15. Carda M., González F., Castillo E., Rodríguez S., Marco J.A. Eur. J. Org. Chem. 2002;2649-2655.
16. Murga J., Falomir E., García-Fortanet J., Carda M., Marco J.A. Org. Lett. 4:2002;3447-3449.
17. Carda M., Rodríguez S., Castillo E., Bellido A., Díaz-Oltra S., Marco J.A. Tetrahedron. 59:2003;857-864.
18. Coppola G.M., Schuster H.F. α-Hydroxy Acids in Enantioselective Synthesis. 1997;95-109 VCH, Weinheim.
19. Ramachandran P.V., Chen G.-M., Brown H.C. Tetrahedron Lett. 38:1997;2417-2420.
20. For a recent review on asymmetric allylborations: Ramachandran P.V. Aldrichim. Acta. 35:2002;23-35.
21. Greene T.W., Wuts P.G.M. Protective Groups in Organic Synthesis. 3rd ed. 1999;113-148 John Wiley and Sons, New York.
22. In anticipation of unsatisfactory diastereoselectivities in reactions of aldehyde 7 with standard ethynylating reagents such as ethynylmagnesium bromide (as turned out to be the case), we envisaged the oxidation of the resulting alcohols (8+epimer) to a conjugated ynone, followed by stereoselective reduction. Since a free β-hydroxy carbonyl group might be convenient for that purpose, we placed an easily cleavable silyl group (TES) at this position.
23. Frantz, D. E.; Fässler, R.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806-1807. In addition to trimethylsilylacetylene, we also used 2-methyl-3-butyn-2-ol: Boyall, D.; López, F.; Sasaki, H.; Frantz, D.; Carreira, E. M. Org. Lett. 2000, 2, 4233-4236. However, whereas the addition step was successful, all attempts to cleave the acetone fragment only led to decomposition.
24. Aside from the contributions of Carreira's group, we have found only a few examples of the use of their asymmetric ethynylation methodology: (a) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855-3858; (b) Maezaki, N.; Kojima, N.; Asai, M.; Tominaga, H.; Tanaka, T. Org. Lett. 2002, 4, 2977-2980; (c) Amador, M.; Ariza, X.; García, J.; Ortiz, J. Tetrahedron Lett. 2002, 43, 2691-2694. For a failure, see: Gung, B. W.; Dickson, H. D.; Seggerson, S.; Bluhm, K. Synth. Commun. 2002, 32, 2733-2740.
25. Aside from the contributions of Carreira's group, we have found only a few examples of the use of their asymmetric ethynylation methodology: (a) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855-3858; (b) Maezaki, N.; Kojima, N.; Asai, M.; Tominaga, H.; Tanaka, T. Org. Lett. 2002, 4, 2977-2980; (c) Amador, M.; Ariza, X.; García, J.; Ortiz, J. Tetrahedron Lett. 2002, 43, 2691-2694. For a failure, see: Gung, B. W.; Dickson, H. D.; Seggerson, S.; Bluhm, K. Synth. Commun. 2002, 32, 2733-2740.
26. Aside from the contributions of Carreira's group, we have found only a few examples of the use of their asymmetric ethynylation methodology: (a) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855-3858; (b) Maezaki, N.; Kojima, N.; Asai, M.; Tominaga, H.; Tanaka, T. Org. Lett. 2002, 4, 2977-2980; (c) Amador, M.; Ariza, X.; García, J.; Ortiz, J. Tetrahedron Lett. 2002, 43, 2691-2694. For a failure, see: Gung, B. W.; Dickson, H. D.; Seggerson, S.; Bluhm, K. Synth. Commun. 2002, 32, 2733-2740.
27. Aside from the contributions of Carreira's group, we have found only a few examples of the use of their asymmetric ethynylation methodology: (a) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855-3858; (b) Maezaki, N.; Kojima, N.; Asai, M.; Tominaga, H.; Tanaka, T. Org. Lett. 2002, 4, 2977-2980; (c) Amador, M.; Ariza, X.; García, J.; Ortiz, J. Tetrahedron Lett. 2002, 43, 2691-2694. For a failure, see: Gung, B. W.; Dickson, H. D.; Seggerson, S.; Bluhm, K. Synth. Commun. 2002, 32, 2733-2740.
28. Further related enantioselective ethynylation methodologies have been recently reported. See, for example: (a) Lu, G.; Li, X. S.; Zhou, Z. Y.; Chan, W. L.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 2147-2152; (b) Jiang, B.; Chen, Z. L.; Xiong, W. N. Chem. Commun. 2002, 1524-1525.
29. Further related enantioselective ethynylation methodologies have been recently reported. See, for example: (a) Lu, G.; Li, X. S.; Zhou, Z. Y.; Chan, W. L.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 2147-2152; (b) Jiang, B.; Chen, Z. L.; Xiong, W. N. Chem. Commun. 2002, 1524-1525.
30. Fürstner A. Angew. Chem., Int. Ed. 39:2000;3012-3043.
31. Trnka T., Grubbs R.H. Acc. Chem. Res. 34:2001;18-29.
32. Fürstner A., Langemann K. J. Am. Chem. Soc. 119:1997;9130-9136.
33. 4b.