Diastereoselective radical addition as a key-step in the synthesis of tetrahydrolipstatin

Journal of the Brazilian Chemical Society

Volumn 7, Issue 5, 1996, Pages 243-246

  Giese, Bernd ^a   Roth, Martin ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

Allylic strain; Stereoselective radical addition; Tetrahydrolipstatin

Indexed keywords

EID: 0030487122     PISSN: 01035053     EISSN: None     Source Type: Journal    
DOI: 10.5935/0103-5053.19960050     Document Type: Article

References (19)

1. Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1996.
2. Bulliard, M.; Zeitz, H.-G.; Giese, B. Synlelt 1991, 423.
3. For other syntheses of tetrahydrolipstatin see: a) Barbier, P.; Schneider, F. Helv. Chim. Acta 70, 196 (1987); b) Barbier, P.; Schneider, F.; and Widmer, U. Helv. Chim. Acta 1987, 70, 1412; c) Pons, J.M.; Kociensky, P. Tetrahedron Lett. 1989, 30, 1833; d) Fleming, I.; Lawrence, N.J. Tetrahedron Lett. 1990, 31, 3645; e) Case-Green, S.C.; Davies, S.G.; Hedgecock, C.J.R. Synlett 1991, 781; f) Chadha, N.K.; Batcho, A.D.; Tang, P.C.; Courtney, L.F.; Cook, C.M.; Wovkulich, P.M.; Uskokovic, M.R. J. Org. Chem. 1991, 56, 4714; g) Hanessian, S.; Tehim, A.; Chen, P. J. Org. Chem. 1993, 58, 7768.
4. For other syntheses of tetrahydrolipstatin see: a) Barbier, P.; Schneider, F. Helv. Chim. Acta 70, 196 (1987); b) Barbier, P.; Schneider, F.; and Widmer, U. Helv. Chim. Acta 1987, 70, 1412; c) Pons, J.M.; Kociensky, P. Tetrahedron Lett. 1989, 30, 1833; d) Fleming, I.; Lawrence, N.J. Tetrahedron Lett. 1990, 31, 3645; e) Case-Green, S.C.; Davies, S.G.; Hedgecock, C.J.R. Synlett 1991, 781; f) Chadha, N.K.; Batcho, A.D.; Tang, P.C.; Courtney, L.F.; Cook, C.M.; Wovkulich, P.M.; Uskokovic, M.R. J. Org. Chem. 1991, 56, 4714; g) Hanessian, S.; Tehim, A.; Chen, P. J. Org. Chem. 1993, 58, 7768.
5. For other syntheses of tetrahydrolipstatin see: a) Barbier, P.; Schneider, F. Helv. Chim. Acta 70, 196 (1987); b) Barbier, P.; Schneider, F.; and Widmer, U. Helv. Chim. Acta 1987, 70, 1412; c) Pons, J.M.; Kociensky, P. Tetrahedron Lett. 1989, 30, 1833; d) Fleming, I.; Lawrence, N.J. Tetrahedron Lett. 1990, 31, 3645; e) Case-Green, S.C.; Davies, S.G.; Hedgecock, C.J.R. Synlett 1991, 781; f) Chadha, N.K.; Batcho, A.D.; Tang, P.C.; Courtney, L.F.; Cook, C.M.; Wovkulich, P.M.; Uskokovic, M.R. J. Org. Chem. 1991, 56, 4714; g) Hanessian, S.; Tehim, A.; Chen, P. J. Org. Chem. 1993, 58, 7768.
6. For other syntheses of tetrahydrolipstatin see: a) Barbier, P.; Schneider, F. Helv. Chim. Acta 70, 196 (1987); b) Barbier, P.; Schneider, F.; and Widmer, U. Helv. Chim. Acta 1987, 70, 1412; c) Pons, J.M.; Kociensky, P. Tetrahedron Lett. 1989, 30, 1833; d) Fleming, I.; Lawrence, N.J. Tetrahedron Lett. 1990, 31, 3645; e) Case-Green, S.C.; Davies, S.G.; Hedgecock, C.J.R. Synlett 1991, 781; f) Chadha, N.K.; Batcho, A.D.; Tang, P.C.; Courtney, L.F.; Cook, C.M.; Wovkulich, P.M.; Uskokovic, M.R. J. Org. Chem. 1991, 56, 4714; g) Hanessian, S.; Tehim, A.; Chen, P. J. Org. Chem. 1993, 58, 7768.
7. For other syntheses of tetrahydrolipstatin see: a) Barbier, P.; Schneider, F. Helv. Chim. Acta 70, 196 (1987); b) Barbier, P.; Schneider, F.; and Widmer, U. Helv. Chim. Acta 1987, 70, 1412; c) Pons, J.M.; Kociensky, P. Tetrahedron Lett. 1989, 30, 1833; d) Fleming, I.; Lawrence, N.J. Tetrahedron Lett. 1990, 31, 3645; e) Case-Green, S.C.; Davies, S.G.; Hedgecock, C.J.R. Synlett 1991, 781; f) Chadha, N.K.; Batcho, A.D.; Tang, P.C.; Courtney, L.F.; Cook, C.M.; Wovkulich, P.M.; Uskokovic, M.R. J. Org. Chem. 1991, 56, 4714; g) Hanessian, S.; Tehim, A.; Chen, P. J. Org. Chem. 1993, 58, 7768.
8. For other syntheses of tetrahydrolipstatin see: a) Barbier, P.; Schneider, F. Helv. Chim. Acta 70, 196 (1987); b) Barbier, P.; Schneider, F.; and Widmer, U. Helv. Chim. Acta 1987, 70, 1412; c) Pons, J.M.; Kociensky, P. Tetrahedron Lett. 1989, 30, 1833; d) Fleming, I.; Lawrence, N.J. Tetrahedron Lett. 1990, 31, 3645; e) Case-Green, S.C.; Davies, S.G.; Hedgecock, C.J.R. Synlett 1991, 781; f) Chadha, N.K.; Batcho, A.D.; Tang, P.C.; Courtney, L.F.; Cook, C.M.; Wovkulich, P.M.; Uskokovic, M.R. J. Org. Chem. 1991, 56, 4714; g) Hanessian, S.; Tehim, A.; Chen, P. J. Org. Chem. 1993, 58, 7768.
9. For other syntheses of tetrahydrolipstatin see: a) Barbier, P.; Schneider, F. Helv. Chim. Acta 70, 196 (1987); b) Barbier, P.; Schneider, F.; and Widmer, U. Helv. Chim. Acta 1987, 70, 1412; c) Pons, J.M.; Kociensky, P. Tetrahedron Lett. 1989, 30, 1833; d) Fleming, I.; Lawrence, N.J. Tetrahedron Lett. 1990, 31, 3645; e) Case-Green, S.C.; Davies, S.G.; Hedgecock, C.J.R. Synlett 1991, 781; f) Chadha, N.K.; Batcho, A.D.; Tang, P.C.; Courtney, L.F.; Cook, C.M.; Wovkulich, P.M.; Uskokovic, M.R. J. Org. Chem. 1991, 56, 4714; g) Hanessian, S.; Tehim, A.; Chen, P. J. Org. Chem. 1993, 58, 7768.
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15. b) Drewes, S.E.; Roos, G.H.P. Tetrahedron 1988, 44, 4653; for a review see: Basavaiah, D.; Rao, P.D.; Hyma, R.S. Tetrahedron 1996, 52, 8001.
16. 2 at 25°C for 12 h.
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19. Giese, B.; Damm, W.; Witzel, T.; Zeitz, H.-G. Tetrahedron Lett. 1993, 34, 7053.