Iterative PD catalyzed additions for a synthesis of methyl 7,8,11,12 tetradehydroretinoate

Tetrahedron Letters

Volumn 37, Issue 23, 1996, Pages 3971-3974

  Trost, Barry M ^a   Harms, Arthur E ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; RETINOIC ACID DERIVATIVE; RETINOID;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029992877     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00726-5     Document Type: Article

References (33)

1. For a few recent overviews, see: Sporn, M.B.; Roberts, A.B.; Goodman, D.S. eds., "The Retinoids: Biology, Chemistry and Medicine," 2nd ed; Raven: New York, 1993; Linney, E. Curr. Top. Dev. Biol. 1992, 27, 309; Bollag, W.; Holdener, E. Ann. Oncol. 1992, 3, 513; Hashimoto, Y.; Shudo, K. Cell. Biol. Rev. 1991, 25, 209; Dawson, M.I.; Okamura, W.H. eds., "Chemistry and Biology of Synthetic Retinoids," CRC Press: Boca Raton, FL, 1990.
2. For a few recent overviews, see: Sporn, M.B.; Roberts, A.B.; Goodman, D.S. eds., "The Retinoids: Biology, Chemistry and Medicine," 2nd ed; Raven: New York, 1993; Linney, E. Curr. Top. Dev. Biol. 1992, 27, 309; Bollag, W.; Holdener, E. Ann. Oncol. 1992, 3, 513; Hashimoto, Y.; Shudo, K. Cell. Biol. Rev. 1991, 25, 209; Dawson, M.I.; Okamura, W.H. eds., "Chemistry and Biology of Synthetic Retinoids," CRC Press: Boca Raton, FL, 1990.
3. For a few recent overviews, see: Sporn, M.B.; Roberts, A.B.; Goodman, D.S. eds., "The Retinoids: Biology, Chemistry and Medicine," 2nd ed; Raven: New York, 1993; Linney, E. Curr. Top. Dev. Biol. 1992, 27, 309; Bollag, W.; Holdener, E. Ann. Oncol. 1992, 3, 513; Hashimoto, Y.; Shudo, K. Cell. Biol. Rev. 1991, 25, 209; Dawson, M.I.; Okamura, W.H. eds., "Chemistry and Biology of Synthetic Retinoids," CRC Press: Boca Raton, FL, 1990.
4. For a few recent overviews, see: Sporn, M.B.; Roberts, A.B.; Goodman, D.S. eds., "The Retinoids: Biology, Chemistry and Medicine," 2nd ed; Raven: New York, 1993; Linney, E. Curr. Top. Dev. Biol. 1992, 27, 309; Bollag, W.; Holdener, E. Ann. Oncol. 1992, 3, 513; Hashimoto, Y.; Shudo, K. Cell. Biol. Rev. 1991, 25, 209; Dawson, M.I.; Okamura, W.H. eds., "Chemistry and Biology of Synthetic Retinoids," CRC Press: Boca Raton, FL, 1990.
5. For a few recent overviews, see: Sporn, M.B.; Roberts, A.B.; Goodman, D.S. eds., "The Retinoids: Biology, Chemistry and Medicine," 2nd ed; Raven: New York, 1993; Linney, E. Curr. Top. Dev. Biol. 1992, 27, 309; Bollag, W.; Holdener, E. Ann. Oncol. 1992, 3, 513; Hashimoto, Y.; Shudo, K. Cell. Biol. Rev. 1991, 25, 209; Dawson, M.I.; Okamura, W.H. eds., "Chemistry and Biology of Synthetic Retinoids," CRC Press: Boca Raton, FL, 1990.
6. Pfahl, M. in "From Molecular Biology to Therapeutics," Bernard, B.A.; Shroot, B. eds.; Karger: Basel, 1993. pp 83-93; Pfahl, M. in "Retinoids: From Basic Science to Clinical Applications," Livrea, M.A.; Vidali, G. eds.; Birkhäuser: Basel, 1994, pp 113-126.
7. Pfahl, M. in "From Molecular Biology to Therapeutics," Bernard, B.A.; Shroot, B. eds.; Karger: Basel, 1993. pp 83-93; Pfahl, M. in "Retinoids: From Basic Science to Clinical Applications," Livrea, M.A.; Vidali, G. eds.; Birkhäuser: Basel, 1994, pp 113-126.
8. Trost, B.M.; McIntosh, M.C. J. Am. Chem. Soc. 1995, 117, 7255; Trost, B.M.; Chan, C; Rühter, G. J. Am. Chem. Soc. 1987, 109, 3486.
9. Trost, B.M.; McIntosh, M.C. J. Am. Chem. Soc. 1995, 117, 7255; Trost, B.M.; Chan, C; Rühter, G. J. Am. Chem. Soc. 1987, 109, 3486.
10. For chemistry and biology of some dehydroretinoids, see Khitrina, L.V.; Eremin, S.V.; Khodonov, A.A.; Kaulen, A.D. Biol. Membr. 1994, 11, 575; Jaeger, E.P.; Jurs, P.C.; Stouch, T.R. Eur. J. Med. Chem. 1993, 28, 275; Sarkar, R.; Das, S.K. Neoplasma 1992, 39, 87; Danshina, S.V.; Drachev, A.L.; Drachev, L.A.; Kaulen, A.D.; Mitsner, B.I.; Khitrina, L.V.; Khodonov, A.A. Bioorg. Khim. 1989, 15, 307; Wuest, H.H.; Janssen, B.; Frickel, F. Biochem. Soc. Trans. 1986, 14, 933; Niculescu-Duvaz, I.; Simon, Z.; Voiculet, N. Carcinogenesis 1985, 6, 479; Hopf, H.; Krause, N. Tetrahedron Lett. 1985, 26, 3323; Gaertner, W.; Oesterhelt, D.; Seifert-Schiller, E.; Towner, P.; Hopf, H.; Boehm, I. J. Am. Chem. Soc. 1984, 106, 5654; Newton, D.L.; Henderson, W.R.; Sporn, M.B. Cancer Res. 1980, 40, 3413; Lotan, R.; Neumann, G.; Lotan, D. Cancer Res. 1980, 40, 1097; Olive, J.L.; Mousseron-Canet, M.; Dornand, J. Bull. Soc. Chim. Fr. 1969, 3247.
11. For chemistry and biology of some dehydroretinoids, see Khitrina, L.V.; Eremin, S.V.; Khodonov, A.A.; Kaulen, A.D. Biol. Membr. 1994, 11, 575; Jaeger, E.P.; Jurs, P.C.; Stouch, T.R. Eur. J. Med. Chem. 1993, 28, 275; Sarkar, R.; Das, S.K. Neoplasma 1992, 39, 87; Danshina, S.V.; Drachev, A.L.; Drachev, L.A.; Kaulen, A.D.; Mitsner, B.I.; Khitrina, L.V.; Khodonov, A.A. Bioorg. Khim. 1989, 15, 307; Wuest, H.H.; Janssen, B.; Frickel, F. Biochem. Soc. Trans. 1986, 14, 933; Niculescu-Duvaz, I.; Simon, Z.; Voiculet, N. Carcinogenesis 1985, 6, 479; Hopf, H.; Krause, N. Tetrahedron Lett. 1985, 26, 3323; Gaertner, W.; Oesterhelt, D.; Seifert-Schiller, E.; Towner, P.; Hopf, H.; Boehm, I. J. Am. Chem. Soc. 1984, 106, 5654; Newton, D.L.; Henderson, W.R.; Sporn, M.B. Cancer Res. 1980, 40, 3413; Lotan, R.; Neumann, G.; Lotan, D. Cancer Res. 1980, 40, 1097; Olive, J.L.; Mousseron-Canet, M.; Dornand, J. Bull. Soc. Chim. Fr. 1969, 3247.
12. For chemistry and biology of some dehydroretinoids, see Khitrina, L.V.; Eremin, S.V.; Khodonov, A.A.; Kaulen, A.D. Biol. Membr. 1994, 11, 575; Jaeger, E.P.; Jurs, P.C.; Stouch, T.R. Eur. J. Med. Chem. 1993, 28, 275; Sarkar, R.; Das, S.K. Neoplasma 1992, 39, 87; Danshina, S.V.; Drachev, A.L.; Drachev, L.A.; Kaulen, A.D.; Mitsner, B.I.; Khitrina, L.V.; Khodonov, A.A. Bioorg. Khim. 1989, 15, 307; Wuest, H.H.; Janssen, B.; Frickel, F. Biochem. Soc. Trans. 1986, 14, 933; Niculescu-Duvaz, I.; Simon, Z.; Voiculet, N. Carcinogenesis 1985, 6, 479; Hopf, H.; Krause, N. Tetrahedron Lett. 1985, 26, 3323; Gaertner, W.; Oesterhelt, D.; Seifert-Schiller, E.; Towner, P.; Hopf, H.; Boehm, I. J. Am. Chem. Soc. 1984, 106, 5654; Newton, D.L.; Henderson, W.R.; Sporn, M.B. Cancer Res. 1980, 40, 3413; Lotan, R.; Neumann, G.; Lotan, D. Cancer Res. 1980, 40, 1097; Olive, J.L.; Mousseron-Canet, M.; Dornand, J. Bull. Soc. Chim. Fr. 1969, 3247.
13. For chemistry and biology of some dehydroretinoids, see Khitrina, L.V.; Eremin, S.V.; Khodonov, A.A.; Kaulen, A.D. Biol. Membr. 1994, 11, 575; Jaeger, E.P.; Jurs, P.C.; Stouch, T.R. Eur. J. Med. Chem. 1993, 28, 275; Sarkar, R.; Das, S.K. Neoplasma 1992, 39, 87; Danshina, S.V.; Drachev, A.L.; Drachev, L.A.; Kaulen, A.D.; Mitsner, B.I.; Khitrina, L.V.; Khodonov, A.A. Bioorg. Khim. 1989, 15, 307; Wuest, H.H.; Janssen, B.; Frickel, F. Biochem. Soc. Trans. 1986, 14, 933; Niculescu-Duvaz, I.; Simon, Z.; Voiculet, N. Carcinogenesis 1985, 6, 479; Hopf, H.; Krause, N. Tetrahedron Lett. 1985, 26, 3323; Gaertner, W.; Oesterhelt, D.; Seifert-Schiller, E.; Towner, P.; Hopf, H.; Boehm, I. J. Am. Chem. Soc. 1984, 106, 5654; Newton, D.L.; Henderson, W.R.; Sporn, M.B. Cancer Res. 1980, 40, 3413; Lotan, R.; Neumann, G.; Lotan, D. Cancer Res. 1980, 40, 1097; Olive, J.L.; Mousseron-Canet, M.; Dornand, J. Bull. Soc. Chim. Fr. 1969, 3247.
14. For chemistry and biology of some dehydroretinoids, see Khitrina, L.V.; Eremin, S.V.; Khodonov, A.A.; Kaulen, A.D. Biol. Membr. 1994, 11, 575; Jaeger, E.P.; Jurs, P.C.; Stouch, T.R. Eur. J. Med. Chem. 1993, 28, 275; Sarkar, R.; Das, S.K. Neoplasma 1992, 39, 87; Danshina, S.V.; Drachev, A.L.; Drachev, L.A.; Kaulen, A.D.; Mitsner, B.I.; Khitrina, L.V.; Khodonov, A.A. Bioorg. Khim. 1989, 15, 307; Wuest, H.H.; Janssen, B.; Frickel, F. Biochem. Soc. Trans. 1986, 14, 933; Niculescu-Duvaz, I.; Simon, Z.; Voiculet, N. Carcinogenesis 1985, 6, 479; Hopf, H.; Krause, N. Tetrahedron Lett. 1985, 26, 3323; Gaertner, W.; Oesterhelt, D.; Seifert-Schiller, E.; Towner, P.; Hopf, H.; Boehm, I. J. Am. Chem. Soc. 1984, 106, 5654; Newton, D.L.; Henderson, W.R.; Sporn, M.B. Cancer Res. 1980, 40, 3413; Lotan, R.; Neumann, G.; Lotan, D. Cancer Res. 1980, 40, 1097; Olive, J.L.; Mousseron-Canet, M.; Dornand, J. Bull. Soc. Chim. Fr. 1969, 3247.
15. For chemistry and biology of some dehydroretinoids, see Khitrina, L.V.; Eremin, S.V.; Khodonov, A.A.; Kaulen, A.D. Biol. Membr. 1994, 11, 575; Jaeger, E.P.; Jurs, P.C.; Stouch, T.R. Eur. J. Med. Chem. 1993, 28, 275; Sarkar, R.; Das, S.K. Neoplasma 1992, 39, 87; Danshina, S.V.; Drachev, A.L.; Drachev, L.A.; Kaulen, A.D.; Mitsner, B.I.; Khitrina, L.V.; Khodonov, A.A. Bioorg. Khim. 1989, 15, 307; Wuest, H.H.; Janssen, B.; Frickel, F. Biochem. Soc. Trans. 1986, 14, 933; Niculescu-Duvaz, I.; Simon, Z.; Voiculet, N. Carcinogenesis 1985, 6, 479; Hopf, H.; Krause, N. Tetrahedron Lett. 1985, 26, 3323; Gaertner, W.; Oesterhelt, D.; Seifert-Schiller, E.; Towner, P.; Hopf, H.; Boehm, I. J. Am. Chem. Soc. 1984, 106, 5654; Newton, D.L.; Henderson, W.R.; Sporn, M.B. Cancer Res. 1980, 40, 3413; Lotan, R.; Neumann, G.; Lotan, D. Cancer Res. 1980, 40, 1097; Olive, J.L.; Mousseron-Canet, M.; Dornand, J. Bull. Soc. Chim. Fr. 1969, 3247.
16. For chemistry and biology of some dehydroretinoids, see Khitrina, L.V.; Eremin, S.V.; Khodonov, A.A.; Kaulen, A.D. Biol. Membr. 1994, 11, 575; Jaeger, E.P.; Jurs, P.C.; Stouch, T.R. Eur. J. Med. Chem. 1993, 28, 275; Sarkar, R.; Das, S.K. Neoplasma 1992, 39, 87; Danshina, S.V.; Drachev, A.L.; Drachev, L.A.; Kaulen, A.D.; Mitsner, B.I.; Khitrina, L.V.; Khodonov, A.A. Bioorg. Khim. 1989, 15, 307; Wuest, H.H.; Janssen, B.; Frickel, F. Biochem. Soc. Trans. 1986, 14, 933; Niculescu-Duvaz, I.; Simon, Z.; Voiculet, N. Carcinogenesis 1985, 6, 479; Hopf, H.; Krause, N. Tetrahedron Lett. 1985, 26, 3323; Gaertner, W.; Oesterhelt, D.; Seifert-Schiller, E.; Towner, P.; Hopf, H.; Boehm, I. J. Am. Chem. Soc. 1984, 106, 5654; Newton, D.L.; Henderson, W.R.; Sporn, M.B. Cancer Res. 1980, 40, 3413; Lotan, R.; Neumann, G.; Lotan, D. Cancer Res. 1980, 40, 1097; Olive, J.L.; Mousseron-Canet, M.; Dornand, J. Bull. Soc. Chim. Fr. 1969, 3247.
17. For chemistry and biology of some dehydroretinoids, see Khitrina, L.V.; Eremin, S.V.; Khodonov, A.A.; Kaulen, A.D. Biol. Membr. 1994, 11, 575; Jaeger, E.P.; Jurs, P.C.; Stouch, T.R. Eur. J. Med. Chem. 1993, 28, 275; Sarkar, R.; Das, S.K. Neoplasma 1992, 39, 87; Danshina, S.V.; Drachev, A.L.; Drachev, L.A.; Kaulen, A.D.; Mitsner, B.I.; Khitrina, L.V.; Khodonov, A.A. Bioorg. Khim. 1989, 15, 307; Wuest, H.H.; Janssen, B.; Frickel, F. Biochem. Soc. Trans. 1986, 14, 933; Niculescu-Duvaz, I.; Simon, Z.; Voiculet, N. Carcinogenesis 1985, 6, 479; Hopf, H.; Krause, N. Tetrahedron Lett. 1985, 26, 3323; Gaertner, W.; Oesterhelt, D.; Seifert-Schiller, E.; Towner, P.; Hopf, H.; Boehm, I. J. Am. Chem. Soc. 1984, 106, 5654; Newton, D.L.; Henderson, W.R.; Sporn, M.B. Cancer Res. 1980, 40, 3413; Lotan, R.; Neumann, G.; Lotan, D. Cancer Res. 1980, 40, 1097; Olive, J.L.; Mousseron-Canet, M.; Dornand, J. Bull. Soc. Chim. Fr. 1969, 3247.
18. For chemistry and biology of some dehydroretinoids, see Khitrina, L.V.; Eremin, S.V.; Khodonov, A.A.; Kaulen, A.D. Biol. Membr. 1994, 11, 575; Jaeger, E.P.; Jurs, P.C.; Stouch, T.R. Eur. J. Med. Chem. 1993, 28, 275; Sarkar, R.; Das, S.K. Neoplasma 1992, 39, 87; Danshina, S.V.; Drachev, A.L.; Drachev, L.A.; Kaulen, A.D.; Mitsner, B.I.; Khitrina, L.V.; Khodonov, A.A. Bioorg. Khim. 1989, 15, 307; Wuest, H.H.; Janssen, B.; Frickel, F. Biochem. Soc. Trans. 1986, 14, 933; Niculescu-Duvaz, I.; Simon, Z.; Voiculet, N. Carcinogenesis 1985, 6, 479; Hopf, H.; Krause, N. Tetrahedron Lett. 1985, 26, 3323; Gaertner, W.; Oesterhelt, D.; Seifert-Schiller, E.; Towner, P.; Hopf, H.; Boehm, I. J. Am. Chem. Soc. 1984, 106, 5654; Newton, D.L.; Henderson, W.R.; Sporn, M.B. Cancer Res. 1980, 40, 3413; Lotan, R.; Neumann, G.; Lotan, D. Cancer Res. 1980, 40, 1097; Olive, J.L.; Mousseron-Canet, M.; Dornand, J. Bull. Soc. Chim. Fr. 1969, 3247.
19. For chemistry and biology of some dehydroretinoids, see Khitrina, L.V.; Eremin, S.V.; Khodonov, A.A.; Kaulen, A.D. Biol. Membr. 1994, 11, 575; Jaeger, E.P.; Jurs, P.C.; Stouch, T.R. Eur. J. Med. Chem. 1993, 28, 275; Sarkar, R.; Das, S.K. Neoplasma 1992, 39, 87; Danshina, S.V.; Drachev, A.L.; Drachev, L.A.; Kaulen, A.D.; Mitsner, B.I.; Khitrina, L.V.; Khodonov, A.A. Bioorg. Khim. 1989, 15, 307; Wuest, H.H.; Janssen, B.; Frickel, F. Biochem. Soc. Trans. 1986, 14, 933; Niculescu-Duvaz, I.; Simon, Z.; Voiculet, N. Carcinogenesis 1985, 6, 479; Hopf, H.; Krause, N. Tetrahedron Lett. 1985, 26, 3323; Gaertner, W.; Oesterhelt, D.; Seifert-Schiller, E.; Towner, P.; Hopf, H.; Boehm, I. J. Am. Chem. Soc. 1984, 106, 5654; Newton, D.L.; Henderson, W.R.; Sporn, M.B. Cancer Res. 1980, 40, 3413; Lotan, R.; Neumann, G.; Lotan, D. Cancer Res. 1980, 40, 1097; Olive, J.L.; Mousseron-Canet, M.; Dornand, J. Bull. Soc. Chim. Fr. 1969, 3247.
20. For chemistry and biology of some dehydroretinoids, see Khitrina, L.V.; Eremin, S.V.; Khodonov, A.A.; Kaulen, A.D. Biol. Membr. 1994, 11, 575; Jaeger, E.P.; Jurs, P.C.; Stouch, T.R. Eur. J. Med. Chem. 1993, 28, 275; Sarkar, R.; Das, S.K. Neoplasma 1992, 39, 87; Danshina, S.V.; Drachev, A.L.; Drachev, L.A.; Kaulen, A.D.; Mitsner, B.I.; Khitrina, L.V.; Khodonov, A.A. Bioorg. Khim. 1989, 15, 307; Wuest, H.H.; Janssen, B.; Frickel, F. Biochem. Soc. Trans. 1986, 14, 933; Niculescu-Duvaz, I.; Simon, Z.; Voiculet, N. Carcinogenesis 1985, 6, 479; Hopf, H.; Krause, N. Tetrahedron Lett. 1985, 26, 3323; Gaertner, W.; Oesterhelt, D.; Seifert-Schiller, E.; Towner, P.; Hopf, H.; Boehm, I. J. Am. Chem. Soc. 1984, 106, 5654; Newton, D.L.; Henderson, W.R.; Sporn, M.B. Cancer Res. 1980, 40, 3413; Lotan, R.; Neumann, G.; Lotan, D. Cancer Res. 1980, 40, 1097; Olive, J.L.; Mousseron-Canet, M.; Dornand, J. Bull. Soc. Chim. Fr. 1969, 3247.
21. Hollinshead, D.M.; Howell, S.C.; Ley, S.V.; Mahon, M.; Ratcliffe, N.M.; Worthington, P.A. J. Chem. Soc. Perkin I 1983, 1549.
22. This compound has been fully characterized spectroscopically and elemental composition established by high resolution mass spectrometry and/or elemental composition.
23. 2: 310.9334. Found: 310.9335.
24. Cf. Haugan, J.A.; Kongsaeree, P.; Clardy, J.; Liaaen-Jensen, S. Tetrahedron: Asymmetry 1994, 5, 1367.
25. Cf Roush, W.R.; Brown, B.B. J. Am. Chem. Soc. 1993, 115, 2268. For applications in retinoid chemistry, see: von Planta, C.; Schwieter, U.; Chopard-dit-Jean, L.; Rüegg, R.; Kofler, M.; Isler, O. Helv. Chim. Acta 1962, 45, 548; Schwieter, U.; Saucy, G.; Montavon, M.; von Planta, C.; Rüegg, R.; Isler, O. Helv. Chim. Acta 1962, 45, 517.
26. Cf Roush, W.R.; Brown, B.B. J. Am. Chem. Soc. 1993, 115, 2268. For applications in retinoid chemistry, see: von Planta, C.; Schwieter, U.; Chopard-dit-Jean, L.; Rüegg, R.; Kofler, M.; Isler, O. Helv. Chim. Acta 1962, 45, 548; Schwieter, U.; Saucy, G.; Montavon, M.; von Planta, C.; Rüegg, R.; Isler, O. Helv. Chim. Acta 1962, 45, 517.
27. Cf Roush, W.R.; Brown, B.B. J. Am. Chem. Soc. 1993, 115, 2268. For applications in retinoid chemistry, see: von Planta, C.; Schwieter, U.; Chopard-dit-Jean, L.; Rüegg, R.; Kofler, M.; Isler, O. Helv. Chim. Acta 1962, 45, 548; Schwieter, U.; Saucy, G.; Montavon, M.; von Planta, C.; Rüegg, R.; Isler, O. Helv. Chim. Acta 1962, 45, 517.
28. Negishi, E.; King, A.O.; Tour, J.M. Org. Syn. 1985, 64, 44.
29. Dess, B.D.; Martin, J.C. J. Am. Chem. Soc. 1991, 113, 7277.
30. Ley, S.V.; Norman, J.; Griffith, W.P.; Marsden, S.P. Synthesis 1994, 639.
31. Corey, E.J.; Fuchs, P.L. Tetrahedron Lett. 1972, 13, 3769.
32. Miwa, K.; Aoyama, T.; Shioiri, T. Synlett 1994, 107.
33. As an example, semihydrogenation, cf Coe, J.W.; Hawes, C.R.; Towers, P. J. Labelled Cmpd. Radiopharm. 1995, 36, 587.