A stereoselective synthesis of (–)-tetrahydrolipstatin

(Note: The full text of this document is currently only available in the PDF Version )

Arun K. Ghosh and Chunfeng Liu


Abstract

A stereoselective synthesis of (–)-tetrahydrolipstatin has been accomplished utilizing olefin metathesis of an acrylate ester as the key step.


References

  1. E. K. Weibel, P. Hadvary, E. Hochuli, E. Kupfer and H. Lengsfeld, J. Antibiot., 1987, 40, 1081 CAS; P. Hadvary, H. Lengsfeld and H. Wolfer, Biochem. J., 1988, 256, 357 CAS.
  2. S. Hogan, A. Fleury, P. Hadvary, H. Lengsfeld, M. K. Meier, J. Triscari and A. C. Sullivan, Int. J. Obes., 1987, 11, 35 (suppl. 3).
  3. P. Hadvary, W. Sidler, W. Meister, W. Vetter and H. Wolfer, J. Biol. Chem., 1991, 266, 2021 CAS.
  4. M. L. Drent and E. A. van der Veen, Obes. Res., 1995, 3(suppl. 4), 623S Search PubMed.
  5. (a) I. Paterson and V. A. Doughty, Tetrahedron Lett., 1999, 40, 393 CrossRef CAS; (b) I. Fleming and N. J. Lawrence, J. Chem. Soc., Perkin Trans. 1, 1998, 2679 RSC; (c) B. Giese and M. J. Roth, J. Braz. Chem. Soc., 1996, 7, 243 Search PubMed; (d) A. Pommier, J. M. Pons, P. J. Kocienski and L. Wong, Synthesis, 1994, 1294 CrossRef CAS; (e) S. Hanessian, A. Tehim and P. Chen, J. Org. Chem., 1993, 58, 7768 CrossRef CAS; (f) S. C. Case-Green, S. G. Davies and C. J. R. Hedgecock, Synlett, 1991, 781 CrossRef CAS; (g) N. K. Chadha, A. D. Batcho, P. C. Tang, L. F. Courtney, C. M. Cook, P. M. Wovkulich and M. R. Uskokovic, J. Org. Chem., 1991, 56, 4714 CrossRef CAS; (h) I. Fleming and N. J. Lawrence, Tetrahedron Lett., 1990, 31, 3645 CrossRef CAS; (i) J. Pons and P. J. Kocienski, Tetrahedron Lett., 1989, 30, 1833 CrossRef CAS; (j) P. Barbier and F. Schneider, J. Org. Chem., 1988, 53, 1218 CrossRef CAS; (k) P. Barbier and F. Schneider, Helv. Chim. Acta, 1987, 70, 196 CAS; (l) P. Barbier, F. Schneider and U. Widmer, Helv. Chim. Acta, 1987, 70, 1412 CAS.
  6. (a) K. C. Nicolaou, R. M. Rodriguez, H. J. Mitchell and F. L. van Delft, Angew. Chem., Int. Ed., 1998, 37, 1874 CrossRef CAS; (b) A. K. Ghosh, J. Cappiello and D. Shin, Tetrahedron Lett., 1998, 39, 4651 CrossRef CAS; (c) J. Cossy, D. Bauer and V. Bellosta, Tetrahedron Lett, 1999, 40, 4187 CrossRef CAS and references cited therein.
  7. For recent reviews, see: (a) D. L. Wright, Curr. Org. Chem., 1999, 3, 211 Search PubMed; (b) R. H. Grubbs and S. Chang, Tetrahedron, 1998, 54, 4413 CrossRef CAS; (c) S. K. Amstrong, J. Chem. Soc., Perkin Trans. 1, 1998, 371 RSC; (d) M. Schuster and S. Blechert, Angew. Chem., Int. Ed. Engl., 1997, 36, 2037 CrossRef CAS and references cited therein.
  8. G. E. Keck, K. H. Tarbet and L. S. Geraci, J. Am. Chem. Soc., 1993, 115, 8467 CrossRef CAS; G. E. Keck and D. Krishnamurthy, Org. Synth., 1997, 75, 12.
  9. J. A. Dale, D. L. Dull and H. S. Mosher, J. Org. Chem., 1969, 34, 2543 CrossRef CAS.
  10. S. Takano, Y. Shimazaki, Y. Sekiguchi and K. Ogasawara, Synthesis, 1989, 539 CrossRef CAS.
  11. M. Miyashita, T. Suzuki and A. Yoshikoshi, Tetrahedron Lett., 1987, 28, 4293 CrossRef CAS; M. Miyashita, M. Hoshino, T. Suzuki and A. Yoshikoshi, Chem. Lett., 1988, 507 CAS.
  12. D. Seebach, J. Aebi and D. Wasmuth, Org. Synth., 1985, 63, 109 CAS.
  13. Alkylation of the corresponding β-hydroxy ester containing an anti-δ-benzyloxy group proceeded with excellent diastereoselectivity (40∶1). [ref. 5(e)]. Thus, the stereochemistry of the remote alkoxy group has little influence on the stereochemical outcome of this alkylation process.
  14. All new compounds gave satisfactory spectroscopic and analytical results.
Click here to see how this site uses Cookies. View our privacy policy here.