Total syntheses of (R)-argentilactone and (R)-goniothalamin via catalytic enantioselective allylation of aldehydes

Tetrahedron Letters

Volumn 44, Issue 48, 2003, Pages 8721-8724

  De Fátima, Ângelo ^a   Pilli, Ronaldo Aloise ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

(R) argentilactone; (R) goniothalamin; Catalytic asymmetric allylation

Indexed keywords

ALDEHYDE DERIVATIVE; ANTILEISHMANIAL AGENT; ANTINEOPLASTIC AGENT; ARGENTILACTONE; CINNAMALDEHYDE; GONIOTHALAMIN; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; GAS CHROMATOGRAPHY; RING CLOSING METATHESIS; STRUCTURE ANALYSIS;

EID: 0142153445     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.122     Document Type: Article

References (45)

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20. For more recently synthesis of (R)-argentilactone, see: (a) Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. J. Ind. Chem. Soc. 1999, 76, 739-742; (b) Saeed, M.; Ilg, T.; Schick, M.; Abbas, M.; Voelter, W. Tetrahedron Lett. 2001, 42, 7401-7403; (c) Hansen, T. V. Tetrahedron: Asymmetry 2002, 13, 547-550. For other synthesis of (R)-argentilactone from chiral starting material or through asymmetric reduction using enzymes or microorganisms, see: (d) O'Connor, B.; Just, G. Tetrahedron Lett. 1986, 27, 5201-5202; (e) Rahman, S. S.; Wakefield, B. J.; Roberts, S. M.; Dowle, M. D. J. Chem. Soc., Chem. Commun. 1989, 303-304; (f) Carretero, J. C.; Ghosez, L. Tetrahedron Lett. 1988, 29, 2059-2062.
21. For more recently synthesis of (R)-argentilactone, see: (a) Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. J. Ind. Chem. Soc. 1999, 76, 739-742; (b) Saeed, M.; Ilg, T.; Schick, M.; Abbas, M.; Voelter, W. Tetrahedron Lett. 2001, 42, 7401-7403; (c) Hansen, T. V. Tetrahedron: Asymmetry 2002, 13, 547-550. For other synthesis of (R)-argentilactone from chiral starting material or through asymmetric reduction using enzymes or microorganisms, see: (d) O'Connor, B.; Just, G. Tetrahedron Lett. 1986, 27, 5201-5202; (e) Rahman, S. S.; Wakefield, B. J.; Roberts, S. M.; Dowle, M. D. J. Chem. Soc., Chem. Commun. 1989, 303-304; (f) Carretero, J. C.; Ghosez, L. Tetrahedron Lett. 1988, 29, 2059-2062.
22. For more recently synthesis of (R)-argentilactone, see: (a) Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. J. Ind. Chem. Soc. 1999, 76, 739-742; (b) Saeed, M.; Ilg, T.; Schick, M.; Abbas, M.; Voelter, W. Tetrahedron Lett. 2001, 42, 7401-7403; (c) Hansen, T. V. Tetrahedron: Asymmetry 2002, 13, 547-550. For other synthesis of (R)-argentilactone from chiral starting material or through asymmetric reduction using enzymes or microorganisms, see: (d) O'Connor, B.; Just, G. Tetrahedron Lett. 1986, 27, 5201-5202; (e) Rahman, S. S.; Wakefield, B. J.; Roberts, S. M.; Dowle, M. D. J. Chem. Soc., Chem. Commun. 1989, 303-304; (f) Carretero, J. C.; Ghosez, L. Tetrahedron Lett. 1988, 29, 2059-2062.
23. For more recently synthesis of (R)-argentilactone, see: (a) Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. J. Ind. Chem. Soc. 1999, 76, 739-742; (b) Saeed, M.; Ilg, T.; Schick, M.; Abbas, M.; Voelter, W. Tetrahedron Lett. 2001, 42, 7401-7403; (c) Hansen, T. V. Tetrahedron: Asymmetry 2002, 13, 547-550. For other synthesis of (R)-argentilactone from chiral starting material or through asymmetric reduction using enzymes or microorganisms, see: (d) O'Connor, B.; Just, G. Tetrahedron Lett. 1986, 27, 5201-5202; (e) Rahman, S. S.; Wakefield, B. J.; Roberts, S. M.; Dowle, M. D. J. Chem. Soc., Chem. Commun. 1989, 303-304; (f) Carretero, J. C.; Ghosez, L. Tetrahedron Lett. 1988, 29, 2059-2062.
24. For more recently synthesis of (R)-argentilactone, see: (a) Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. J. Ind. Chem. Soc. 1999, 76, 739-742; (b) Saeed, M.; Ilg, T.; Schick, M.; Abbas, M.; Voelter, W. Tetrahedron Lett. 2001, 42, 7401-7403; (c) Hansen, T. V. Tetrahedron: Asymmetry 2002, 13, 547-550. For other synthesis of (R)-argentilactone from chiral starting material or through asymmetric reduction using enzymes or microorganisms, see: (d) O'Connor, B.; Just, G. Tetrahedron Lett. 1986, 27, 5201-5202; (e) Rahman, S. S.; Wakefield, B. J.; Roberts, S. M.; Dowle, M. D. J. Chem. Soc., Chem. Commun. 1989, 303-304; (f) Carretero, J. C.; Ghosez, L. Tetrahedron Lett. 1988, 29, 2059-2062.
25. For more recently synthesis of (R)-argentilactone, see: (a) Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. J. Ind. Chem. Soc. 1999, 76, 739-742; (b) Saeed, M.; Ilg, T.; Schick, M.; Abbas, M.; Voelter, W. Tetrahedron Lett. 2001, 42, 7401-7403; (c) Hansen, T. V. Tetrahedron: Asymmetry 2002, 13, 547-550. For other synthesis of (R)-argentilactone from chiral starting material or through asymmetric reduction using enzymes or microorganisms, see: (d) O'Connor, B.; Just, G. Tetrahedron Lett. 1986, 27, 5201-5202; (e) Rahman, S. S.; Wakefield, B. J.; Roberts, S. M.; Dowle, M. D. J. Chem. Soc., Chem. Commun. 1989, 303-304; (f) Carretero, J. C.; Ghosez, L. Tetrahedron Lett. 1988, 29, 2059-2062.
26. For more recently synthesis of (R)-goniothalamin, see: (a) Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586; (b) Peng, X. S.; Li, A. P.; Shen, H.; Wu, T. X.; Pan, X. F. J. Chem. Res. 2002, 7, 330-332; (c) Tsubuki, M.; Honda, T. Heterocycles 1993, 35, 281-288; (d) Fátima, A.; Pilli, R. A. Arkivoc. 2003, 10, 118-126. For other synthesis of (R)-goniothalamin from chiral starting material or through asymmetric reduction using enzymes or microorganisms, see: (e) Bennett, F.; Knight, D. W. Tetrahedron Lett. 1988, 29, 4625-4628; (f) Fuganti, C.; Pedrocchi-Fantoni, G.; Sarra, A.; Servi, S. Tetrahedron: Asymmetry 1994, 5, 1135-1138; (g) Henkel, B.; Kunath, A. Schick, H. Liebigs Ann. Chem. 1992, 809-811; (h) Bennett, F.; Knight, D. W.; Fenton, G. J. Chem. Soc., Perkin. Trans. 1 1991, 519-523.
27. For more recently synthesis of (R)-goniothalamin, see: (a) Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586; (b) Peng, X. S.; Li, A. P.; Shen, H.; Wu, T. X.; Pan, X. F. J. Chem. Res. 2002, 7, 330-332; (c) Tsubuki, M.; Honda, T. Heterocycles 1993, 35, 281-288; (d) Fátima, A.; Pilli, R. A. Arkivoc. 2003, 10, 118-126. For other synthesis of (R)-goniothalamin from chiral starting material or through asymmetric reduction using enzymes or microorganisms, see: (e) Bennett, F.; Knight, D. W. Tetrahedron Lett. 1988, 29, 4625-4628; (f) Fuganti, C.; Pedrocchi-Fantoni, G.; Sarra, A.; Servi, S. Tetrahedron: Asymmetry 1994, 5, 1135-1138; (g) Henkel, B.; Kunath, A. Schick, H. Liebigs Ann. Chem. 1992, 809-811; (h) Bennett, F.; Knight, D. W.; Fenton, G. J. Chem. Soc., Perkin. Trans. 1 1991, 519-523.
28. For more recently synthesis of (R)-goniothalamin, see: (a) Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586; (b) Peng, X. S.; Li, A. P.; Shen, H.; Wu, T. X.; Pan, X. F. J. Chem. Res. 2002, 7, 330-332; (c) Tsubuki, M.; Honda, T. Heterocycles 1993, 35, 281-288; (d) Fátima, A.; Pilli, R. A. Arkivoc. 2003, 10, 118-126. For other synthesis of (R)-goniothalamin from chiral starting material or through asymmetric reduction using enzymes or microorganisms, see: (e) Bennett, F.; Knight, D. W. Tetrahedron Lett. 1988, 29, 4625-4628; (f) Fuganti, C.; Pedrocchi-Fantoni, G.; Sarra, A.; Servi, S. Tetrahedron: Asymmetry 1994, 5, 1135-1138; (g) Henkel, B.; Kunath, A. Schick, H. Liebigs Ann. Chem. 1992, 809-811; (h) Bennett, F.; Knight, D. W.; Fenton, G. J. Chem. Soc., Perkin. Trans. 1 1991, 519-523.
29. For more recently synthesis of (R)-goniothalamin, see: (a) Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586; (b) Peng, X. S.; Li, A. P.; Shen, H.; Wu, T. X.; Pan, X. F. J. Chem. Res. 2002, 7, 330-332; (c) Tsubuki, M.; Honda, T. Heterocycles 1993, 35, 281-288; (d) Fátima, A.; Pilli, R. A. Arkivoc. 2003, 10, 118-126. For other synthesis of (R)-goniothalamin from chiral starting material or through asymmetric reduction using enzymes or microorganisms, see: (e) Bennett, F.; Knight, D. W. Tetrahedron Lett. 1988, 29, 4625-4628; (f) Fuganti, C.; Pedrocchi-Fantoni, G.; Sarra, A.; Servi, S. Tetrahedron: Asymmetry 1994, 5, 1135-1138; (g) Henkel, B.; Kunath, A. Schick, H. Liebigs Ann. Chem. 1992, 809-811; (h) Bennett, F.; Knight, D. W.; Fenton, G. J. Chem. Soc., Perkin. Trans. 1 1991, 519-523.
30. For more recently synthesis of (R)-goniothalamin, see: (a) Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586; (b) Peng, X. S.; Li, A. P.; Shen, H.; Wu, T. X.; Pan, X. F. J. Chem. Res. 2002, 7, 330-332; (c) Tsubuki, M.; Honda, T. Heterocycles 1993, 35, 281-288; (d) Fátima, A.; Pilli, R. A. Arkivoc. 2003, 10, 118-126. For other synthesis of (R)-goniothalamin from chiral starting material or through asymmetric reduction using enzymes or microorganisms, see: (e) Bennett, F.; Knight, D. W. Tetrahedron Lett. 1988, 29, 4625-4628; (f) Fuganti, C.; Pedrocchi-Fantoni, G.; Sarra, A.; Servi, S. Tetrahedron: Asymmetry 1994, 5, 1135-1138; (g) Henkel, B.; Kunath, A. Schick, H. Liebigs Ann. Chem. 1992, 809-811; (h) Bennett, F.; Knight, D. W.; Fenton, G. J. Chem. Soc., Perkin. Trans. 1 1991, 519-523.
31. For more recently synthesis of (R)-goniothalamin, see: (a) Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586; (b) Peng, X. S.; Li, A. P.; Shen, H.; Wu, T. X.; Pan, X. F. J. Chem. Res. 2002, 7, 330-332; (c) Tsubuki, M.; Honda, T. Heterocycles 1993, 35, 281-288; (d) Fátima, A.; Pilli, R. A. Arkivoc. 2003, 10, 118-126. For other synthesis of (R)-goniothalamin from chiral starting material or through asymmetric reduction using enzymes or microorganisms, see: (e) Bennett, F.; Knight, D. W. Tetrahedron Lett. 1988, 29, 4625-4628; (f) Fuganti, C.; Pedrocchi-Fantoni, G.; Sarra, A.; Servi, S. Tetrahedron: Asymmetry 1994, 5, 1135-1138; (g) Henkel, B.; Kunath, A. Schick, H. Liebigs Ann. Chem. 1992, 809-811; (h) Bennett, F.; Knight, D. W.; Fenton, G. J. Chem. Soc., Perkin. Trans. 1 1991, 519-523.
32. For more recently synthesis of (R)-goniothalamin, see: (a) Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586; (b) Peng, X. S.; Li, A. P.; Shen, H.; Wu, T. X.; Pan, X. F. J. Chem. Res. 2002, 7, 330-332; (c) Tsubuki, M.; Honda, T. Heterocycles 1993, 35, 281-288; (d) Fátima, A.; Pilli, R. A. Arkivoc. 2003, 10, 118-126. For other synthesis of (R)-goniothalamin from chiral starting material or through asymmetric reduction using enzymes or microorganisms, see: (e) Bennett, F.; Knight, D. W. Tetrahedron Lett. 1988, 29, 4625-4628; (f) Fuganti, C.; Pedrocchi-Fantoni, G.; Sarra, A.; Servi, S. Tetrahedron: Asymmetry 1994, 5, 1135-1138; (g) Henkel, B.; Kunath, A. Schick, H. Liebigs Ann. Chem. 1992, 809-811; (h) Bennett, F.; Knight, D. W.; Fenton, G. J. Chem. Soc., Perkin. Trans. 1 1991, 519-523.
33. For more recently synthesis of (R)-goniothalamin, see: (a) Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583-586; (b) Peng, X. S.; Li, A. P.; Shen, H.; Wu, T. X.; Pan, X. F. J. Chem. Res. 2002, 7, 330-332; (c) Tsubuki, M.; Honda, T. Heterocycles 1993, 35, 281-288; (d) Fátima, A.; Pilli, R. A. Arkivoc. 2003, 10, 118-126. For other synthesis of (R)-goniothalamin from chiral starting material or through asymmetric reduction using enzymes or microorganisms, see: (e) Bennett, F.; Knight, D. W. Tetrahedron Lett. 1988, 29, 4625-4628; (f) Fuganti, C.; Pedrocchi-Fantoni, G.; Sarra, A.; Servi, S. Tetrahedron: Asymmetry 1994, 5, 1135-1138; (g) Henkel, B.; Kunath, A. Schick, H. Liebigs Ann. Chem. 1992, 809-811; (h) Bennett, F.; Knight, D. W.; Fenton, G. J. Chem. Soc., Perkin. Trans. 1 1991, 519-523.
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