Towards the total synthesis of saponaceolides: Synthesis of cis-2,4- disubstituted 3,3-dimethylmethylenecyclohexanes

Angewandte Chemie - International Edition

Volumn 38, Issue 24, 1999, Pages 3662-3664

  Trost, Barry M ^a   Corte, James R ^a   Gudiksen, Mark S ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

C C coupling; Cyclohexanes; Cycloisomerizations; Enynes; Natural products

Indexed keywords

CYCLOHEXANE DERIVATIVE; NATURAL PRODUCT; PALLADIUM; SAPONACEOLIDE A; SAPONACEOLIDE B; UNCLASSIFIED DRUG;

ARTICLE; CIS TRANS ISOMERISM; CYTOTOXICITY; DRUG POTENCY; MOLECULAR MODEL; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033576653     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991216)38:24<3662::AID-ANIE3662>3.0.CO;2-1     Document Type: Article

References (45)

1. H. Miyake, H. Ito, T. Yoshida, Can. J. Chem. 1997, 75, 734; H. Ito, Y. Miyake, T. Yoshida, Chem. Pharm. Bull. 1995, 43, 1260; F.-J. Marner, W. Krick, B. Gellrich, L. Jaenicke, W. Winter, J. Org. Chem. 1982, 47, 2531; W. Krick, F.-J. Marner, L. Jaenicke, Helv. Chim. Acta 1984, 67, 318.
2. H. Miyake, H. Ito, T. Yoshida, Can. J. Chem. 1997, 75, 734; H. Ito, Y. Miyake, T. Yoshida, Chem. Pharm. Bull. 1995, 43, 1260; F.-J. Marner, W. Krick, B. Gellrich, L. Jaenicke, W. Winter, J. Org. Chem. 1982, 47, 2531; W. Krick, F.-J. Marner, L. Jaenicke, Helv. Chim. Acta 1984, 67, 318.
3. H. Miyake, H. Ito, T. Yoshida, Can. J. Chem. 1997, 75, 734; H. Ito, Y. Miyake, T. Yoshida, Chem. Pharm. Bull. 1995, 43, 1260; F.-J. Marner, W. Krick, B. Gellrich, L. Jaenicke, W. Winter, J. Org. Chem. 1982, 47, 2531; W. Krick, F.-J. Marner, L. Jaenicke, Helv. Chim. Acta 1984, 67, 318.
4. H. Miyake, H. Ito, T. Yoshida, Can. J. Chem. 1997, 75, 734; H. Ito, Y. Miyake, T. Yoshida, Chem. Pharm. Bull. 1995, 43, 1260; F.-J. Marner, W. Krick, B. Gellrich, L. Jaenicke, W. Winter, J. Org. Chem. 1982, 47, 2531; W. Krick, F.-J. Marner, L. Jaenicke, Helv. Chim. Acta 1984, 67, 318.
5. O. B. Weeks, A. R. Montes, A. G. Andrewes, J. Bacteriol. 1980, 141, 1272; S. Hertzberg, S. Liaaen-Lensen, Acta Chem. Scand. 1977, 31, 215.
6. O. B. Weeks, A. R. Montes, A. G. Andrewes, J. Bacteriol. 1980, 141, 1272; S. Hertzberg, S. Liaaen-Lensen, Acta Chem. Scand. 1977, 31, 215.
7. Z. Pang, K. E. Berquist, O. Sterner, Acta Chem. Scand. 1994, 48, 453; C. Geraci, M. Piattelli, C. Tringali, Magn. Reson. Chem. 1991, 29, 603; M. De Bernardi, L. Garlaschelli, L. Toma, G. Vidari, P. Vita Finzi, Tetrahedron 1991, 47, 7109; M. De Bernardi, L. Garlaschelli, G. Gatti, G. Vidari, P. Vita Finzi, Tetrahedron 1988, 44, 235.
8. Z. Pang, K. E. Berquist, O. Sterner, Acta Chem. Scand. 1994, 48, 453; C. Geraci, M. Piattelli, C. Tringali, Magn. Reson. Chem. 1991, 29, 603; M. De Bernardi, L. Garlaschelli, L. Toma, G. Vidari, P. Vita Finzi, Tetrahedron 1991, 47, 7109; M. De Bernardi, L. Garlaschelli, G. Gatti, G. Vidari, P. Vita Finzi, Tetrahedron 1988, 44, 235.
9. Z. Pang, K. E. Berquist, O. Sterner, Acta Chem. Scand. 1994, 48, 453; C. Geraci, M. Piattelli, C. Tringali, Magn. Reson. Chem. 1991, 29, 603; M. De Bernardi, L. Garlaschelli, L. Toma, G. Vidari, P. Vita Finzi, Tetrahedron 1991, 47, 7109; M. De Bernardi, L. Garlaschelli, G. Gatti, G. Vidari, P. Vita Finzi, Tetrahedron 1988, 44, 235.
10. Z. Pang, K. E. Berquist, O. Sterner, Acta Chem. Scand. 1994, 48, 453; C. Geraci, M. Piattelli, C. Tringali, Magn. Reson. Chem. 1991, 29, 603; M. De Bernardi, L. Garlaschelli, L. Toma, G. Vidari, P. Vita Finzi, Tetrahedron 1991, 47, 7109; M. De Bernardi, L. Garlaschelli, G. Gatti, G. Vidari, P. Vita Finzi, Tetrahedron 1988, 44, 235.
11. G. Vidari, G. Lanfranchi, P. Sartori, S. Serra, Tetrahedron: Asymmetry 1995, 6, 2977.
12. M. Lanz, B. Bartels, H. Pfander, Helv. Chim. Acta 1997, 80, 804; H. Monti, G. Audran, J.-P. Monti, G. Leandri, J. Org. Chem. 1996, 61, 6021; C. Chapius, R. Brauchli, Helv. Chim. Acta. 1993, 76, 2070; J. P. Ferezou, M. Julia, Tetrahedron 1990, 46, 475; C. Nussbaumer, G. Frater, Helv. Chim. Acta 1988, 71, 619; F. Leyendecker, M. T. Comte, Tetrahedron 1987, 43, 85; T. Kawanobe, M. Iwamoto, K. Kozami, M. Matsui, Agric. Biol. Chem. 1987, 51, 791; T. Kitahara, K. Tanida, K. Mori, Agric. Biol. Chem. 1983, 47, 581.
13. M. Lanz, B. Bartels, H. Pfander, Helv. Chim. Acta 1997, 80, 804; H. Monti, G. Audran, J.-P. Monti, G. Leandri, J. Org. Chem. 1996, 61, 6021; C. Chapius, R. Brauchli, Helv. Chim. Acta. 1993, 76, 2070; J. P. Ferezou, M. Julia, Tetrahedron 1990, 46, 475; C. Nussbaumer, G. Frater, Helv. Chim. Acta 1988, 71, 619; F. Leyendecker, M. T. Comte, Tetrahedron 1987, 43, 85; T. Kawanobe, M. Iwamoto, K. Kozami, M. Matsui, Agric. Biol. Chem. 1987, 51, 791; T. Kitahara, K. Tanida, K. Mori, Agric. Biol. Chem. 1983, 47, 581.
14. M. Lanz, B. Bartels, H. Pfander, Helv. Chim. Acta 1997, 80, 804; H. Monti, G. Audran, J.-P. Monti, G. Leandri, J. Org. Chem. 1996, 61, 6021; C. Chapius, R. Brauchli, Helv. Chim. Acta. 1993, 76, 2070; J. P. Ferezou, M. Julia, Tetrahedron 1990, 46, 475; C. Nussbaumer, G. Frater, Helv. Chim. Acta 1988, 71, 619; F. Leyendecker, M. T. Comte, Tetrahedron 1987, 43, 85; T. Kawanobe, M. Iwamoto, K. Kozami, M. Matsui, Agric. Biol. Chem. 1987, 51, 791; T. Kitahara, K. Tanida, K. Mori, Agric. Biol. Chem. 1983, 47, 581.
15. M. Lanz, B. Bartels, H. Pfander, Helv. Chim. Acta 1997, 80, 804; H. Monti, G. Audran, J.-P. Monti, G. Leandri, J. Org. Chem. 1996, 61, 6021; C. Chapius, R. Brauchli, Helv. Chim. Acta. 1993, 76, 2070; J. P. Ferezou, M. Julia, Tetrahedron 1990, 46, 475; C. Nussbaumer, G. Frater, Helv. Chim. Acta 1988, 71, 619; F. Leyendecker, M. T. Comte, Tetrahedron 1987, 43, 85; T. Kawanobe, M. Iwamoto, K. Kozami, M. Matsui, Agric. Biol. Chem. 1987, 51, 791; T. Kitahara, K. Tanida, K. Mori, Agric. Biol. Chem. 1983, 47, 581.
16. M. Lanz, B. Bartels, H. Pfander, Helv. Chim. Acta 1997, 80, 804; H. Monti, G. Audran, J.-P. Monti, G. Leandri, J. Org. Chem. 1996, 61, 6021; C. Chapius, R. Brauchli, Helv. Chim. Acta. 1993, 76, 2070; J. P. Ferezou, M. Julia, Tetrahedron 1990, 46, 475; C. Nussbaumer, G. Frater, Helv. Chim. Acta 1988, 71, 619; F. Leyendecker, M. T. Comte, Tetrahedron 1987, 43, 85; T. Kawanobe, M. Iwamoto, K. Kozami, M. Matsui, Agric. Biol. Chem. 1987, 51, 791; T. Kitahara, K. Tanida, K. Mori, Agric. Biol. Chem. 1983, 47, 581.
17. M. Lanz, B. Bartels, H. Pfander, Helv. Chim. Acta 1997, 80, 804; H. Monti, G. Audran, J.-P. Monti, G. Leandri, J. Org. Chem. 1996, 61, 6021; C. Chapius, R. Brauchli, Helv. Chim. Acta. 1993, 76, 2070; J. P. Ferezou, M. Julia, Tetrahedron 1990, 46, 475; C. Nussbaumer, G. Frater, Helv. Chim. Acta 1988, 71, 619; F. Leyendecker, M. T. Comte, Tetrahedron 1987, 43, 85; T. Kawanobe, M. Iwamoto, K. Kozami, M. Matsui, Agric. Biol. Chem. 1987, 51, 791; T. Kitahara, K. Tanida, K. Mori, Agric. Biol. Chem. 1983, 47, 581.
18. M. Lanz, B. Bartels, H. Pfander, Helv. Chim. Acta 1997, 80, 804; H. Monti, G. Audran, J.-P. Monti, G. Leandri, J. Org. Chem. 1996, 61, 6021; C. Chapius, R. Brauchli, Helv. Chim. Acta. 1993, 76, 2070; J. P. Ferezou, M. Julia, Tetrahedron 1990, 46, 475; C. Nussbaumer, G. Frater, Helv. Chim. Acta 1988, 71, 619; F. Leyendecker, M. T. Comte, Tetrahedron 1987, 43, 85; T. Kawanobe, M. Iwamoto, K. Kozami, M. Matsui, Agric. Biol. Chem. 1987, 51, 791; T. Kitahara, K. Tanida, K. Mori, Agric. Biol. Chem. 1983, 47, 581.
19. M. Lanz, B. Bartels, H. Pfander, Helv. Chim. Acta 1997, 80, 804; H. Monti, G. Audran, J.-P. Monti, G. Leandri, J. Org. Chem. 1996, 61, 6021; C. Chapius, R. Brauchli, Helv. Chim. Acta. 1993, 76, 2070; J. P. Ferezou, M. Julia, Tetrahedron 1990, 46, 475; C. Nussbaumer, G. Frater, Helv. Chim. Acta 1988, 71, 619; F. Leyendecker, M. T. Comte, Tetrahedron 1987, 43, 85; T. Kawanobe, M. Iwamoto, K. Kozami, M. Matsui, Agric. Biol. Chem. 1987, 51, 791; T. Kitahara, K. Tanida, K. Mori, Agric. Biol. Chem. 1983, 47, 581.
20. G. Vidari, N. Pazzi, G. Lanfranchi, S. Serra, Tetrahedron Lett. 1999, 40, 3067.
21. M. J. Krische, B. M. Trost, Tetrahedron 1998, 54, 3693; B. M. Trost, Y. Li, J. Am. Chem. Soc. 1996, 118, 6625; B. M. Trost, D. L. Romero, F. Rise, J. Am. Chem. Soc. 1994, 116, 4268; B. M. Trost, G. J. Tanoury, M. Lautens, C. Chan, D. T. MacPherson, J. Am. Chem. Soc. 1994, 116, 4255.
22. M. J. Krische, B. M. Trost, Tetrahedron 1998, 54, 3693; B. M. Trost, Y. Li, J. Am. Chem. Soc. 1996, 118, 6625; B. M. Trost, D. L. Romero, F. Rise, J. Am. Chem. Soc. 1994, 116, 4268; B. M. Trost, G. J. Tanoury, M. Lautens, C. Chan, D. T. MacPherson, J. Am. Chem. Soc. 1994, 116, 4255.
23. M. J. Krische, B. M. Trost, Tetrahedron 1998, 54, 3693; B. M. Trost, Y. Li, J. Am. Chem. Soc. 1996, 118, 6625; B. M. Trost, D. L. Romero, F. Rise, J. Am. Chem. Soc. 1994, 116, 4268; B. M. Trost, G. J. Tanoury, M. Lautens, C. Chan, D. T. MacPherson, J. Am. Chem. Soc. 1994, 116, 4255.
24. M. J. Krische, B. M. Trost, Tetrahedron 1998, 54, 3693; B. M. Trost, Y. Li, J. Am. Chem. Soc. 1996, 118, 6625; B. M. Trost, D. L. Romero, F. Rise, J. Am. Chem. Soc. 1994, 116, 4268; B. M. Trost, G. J. Tanoury, M. Lautens, C. Chan, D. T. MacPherson, J. Am. Chem. Soc. 1994, 116, 4255.
25. Review: B. M. Trost, M. J. Krische, Synlett 1998, 1.
26. B. M. Trost, M. Lautens, J. Am. Chem. Soc. 1987, 109, 1469; B. M. Trost, M. Lautens, Tetrahedron 1987, 43, 4817.
27. B. M. Trost, M. Lautens, J. Am. Chem. Soc. 1987, 109, 1469; B. M. Trost, M. Lautens, Tetrahedron 1987, 43, 4817.
28. P. G. McDougal, J. G. Rico, Y.-I. Oh, B. D. Condon, J. Org. Chem. 1986, 51, 3388.
29. Y. Terao, M. Akamatsu, K. Achiwa, Chem. Pharm. Bull. 1991, 39, 823. Also known as lipase PS or lipase P, it is claimed by Amano to be identical to PPS; see R. J. Kazlauskas, A. N. E. Weissfloch, A. T. Rappaport, L. A. Cuccia, J. Org. Chem. 1991, 56, 2656.
30. Y. Terao, M. Akamatsu, K. Achiwa, Chem. Pharm. Bull. 1991, 39, 823. Also known as lipase PS or lipase P, it is claimed by Amano to be identical to PPS; see R. J. Kazlauskas, A. N. E. Weissfloch, A. T. Rappaport, L. A. Cuccia, J. Org. Chem. 1991, 56, 2656.
31. Reviews: Enzyme Catalysis in Organic Synthesis (Eds.: K. Drauz, H. Waldmann), VCH, New York, 1995; T. Itoh, Y. Takagi, H. Tsukube, J. Mol. Catal. B 1997, 3, 261.
32. Reviews: Enzyme Catalysis in Organic Synthesis (Eds.: K. Drauz, H. Waldmann), VCH, New York, 1995; T. Itoh, Y. Takagi, H. Tsukube, J. Mol. Catal. B 1997, 3, 261.
33. Monoacetate 10b was converted into (R)-2,2-dimethyl-3-hydroxymethyl-γ-butyrolactone, which was also prepared from known (R)-2-acetoxymethyl-4-penten-1-ol; see K. Tsuji, Y. Tecao, K. Achiwa, Tetrahedron Lett. 1989, 30, 6189.
34. H. Hopf, I. Bohm, J. Kleinschroth, Org. Synth. 1981, 60, 41.
35. T. Mandai, J. Nokami, T. Yano, Y. Yoshinaga, J. Otera, J. Org. Chem. 1984, 49, 172.
36. O. Arjona, R. Perez-Ossorio, A. Perez-Rubalcaba, M. L. Quiroga, J. Chem. Soc. Perkin Trans. 2 1981, 597.
37. B. M. Trost, P. A. Hipskind, J. Y. L. Chung, C. Chan, Angew. Chem. 1989, 101, 1559; Angew. Chem. Int. Ed. Engl. 1989, 28, 1502; B. M. Trost, J. Y. L. Cung, J. Am. Chem. Soc. 1985, 107, 4586.
38. B. M. Trost, P. A. Hipskind, J. Y. L. Chung, C. Chan, Angew. Chem. 1989, 101, 1559; Angew. Chem. Int. Ed. Engl. 1989, 28, 1502; B. M. Trost, J. Y. L. Cung, J. Am. Chem. Soc. 1985, 107, 4586.
39. B. M. Trost, P. A. Hipskind, J. Y. L. Chung, C. Chan, Angew. Chem. 1989, 101, 1559; Angew. Chem. Int. Ed. Engl. 1989, 28, 1502; B. M. Trost, J. Y. L. Cung, J. Am. Chem. Soc. 1985, 107, 4586.
40. Conditions analogous to those of Grigg et al.: R. Grigg, P. Stevenson, T. Worakun, J. Chem. Soc. Chem. Commun. 1984, 1073.
41. In our case the effect of silver salts on the regioselectivity of the β-hydrogen elimination is opposite that normally observed; see T. Jeffrey, Tetrahedron Lett. 1993, 34, 1133.
42. See: D. H. R. Barton, S. W. McCombie, J. Chem. Soc. Perkin Trans. 1 1975, 1574; K. Pankiewicz, A. Matsuda, K. A. Watanabe, J. Org. Chem. 1982, 47, 485.
43. See: D. H. R. Barton, S. W. McCombie, J. Chem. Soc. Perkin Trans. 1 1975, 1574; K. Pankiewicz, A. Matsuda, K. A. Watanabe, J. Org. Chem. 1982, 47, 485.
44. B. M. Trost, J. R. Corte, Angew. Chem. 1999, 111, 3947-3949; Angew. Chem. Int. Ed. 1999, 38, 3664-3666.
45. B. M. Trost, J. R. Corte, Angew. Chem. 1999, 111, 3947-3949; Angew. Chem. Int. Ed. 1999, 38, 3664-3666.