Total syntheses of (-)-herbertenediol, (-)-mastigophorene A, and (-)- mastigophorene B. Combined utility of chiral bicyclic lactams and chiral aryl oxazolines

Journal of the American Chemical Society

Volumn 121, Issue 12, 1999, Pages 2762-2769

  Degnan, Andrew P ^a   Meyers, A I ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; HERBERTENEDIOL; LACTAM; MASTIGOPHORENE A; MASTIGOPHORENE B; OXAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; DIMERIZATION; HYDROLYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033620428     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja984182x     Document Type: Article

References (51)

1. (a) Matsuo, A.; Yuki, S.; Nakayama, M. Chem. Lett. 1983, 1041.
2. (b) Matsuo, A.; Yuki, S.; Nakayama, M. J. Chem. Soc., Perkin Trans. 1 1986, 701.
3. 1b
4. (a) Fukuyama, Y.; Kiriyama, Y.; Kodama, M. Tetrahedron Lett. 1996, 37, 1261.
5. (b) Harrowven, D. C.; Hannam, J. C. Tetrahedron Lett. 1998, 39, 9573.
6. (c) Eicher, T.; Servet, F.; Speicher, A. Synthesis 1996, 863.
7. Fukuyama, Y.; Asakawa, Y. J. Chem. Soc., Perkin Trans. 1 1991, 2737.
8. 4 These syntheses further support this stereochemical assignment.
9. For reviews on the use of chiral bicyclic lactams in synthesis, see: (a) Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503. (b) Brengel, G. P.; Meyers, A. I. J. Chem. Soc., Chem. Comm. 1997, 1.
10. For reviews on the use of chiral bicyclic lactams in synthesis, see: (a) Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503. (b) Brengel, G. P.; Meyers, A. I. J. Chem. Soc., Chem. Comm. 1997, 1.
11. For applications of the asymmetric oxazoline-mediated Ullmann coupling, see: (a) Meyers, A. I.; Willemsen, J. J. Tetrahedron 1998, 54, 10493. (b) Meyers, A. I.; Willemsen, J. J. J. Chem. Soc., Chem. Commun. 1997, 1573. Meyers, A. I.; Price, A. J. Org. Chem. 1998, 63, 412. (d) Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869. (e) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (f) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (g) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 3061.
12. For applications of the asymmetric oxazoline-mediated Ullmann coupling, see: (a) Meyers, A. I.; Willemsen, J. J. Tetrahedron 1998, 54, 10493. (b) Meyers, A. I.; Willemsen, J. J. J. Chem. Soc., Chem. Commun. 1997, 1573. Meyers, A. I.; Price, A. J. Org. Chem. 1998, 63, 412. (d) Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869. (e) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (f) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (g) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 3061.
13. For applications of the asymmetric oxazoline-mediated Ullmann coupling, see: (a) Meyers, A. I.; Willemsen, J. J. Tetrahedron 1998, 54, 10493. (b) Meyers, A. I.; Willemsen, J. J. J. Chem. Soc., Chem. Commun. 1997, 1573. Meyers, A. I.; Price, A. J. Org. Chem. 1998, 63, 412. (d) Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869. (e) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (f) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (g) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 3061.
14. For applications of the asymmetric oxazoline-mediated Ullmann coupling, see: (a) Meyers, A. I.; Willemsen, J. J. Tetrahedron 1998, 54, 10493. (b) Meyers, A. I.; Willemsen, J. J. J. Chem. Soc., Chem. Commun. 1997, 1573. Meyers, A. I.; Price, A. J. Org. Chem. 1998, 63, 412. Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869. (e) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (f) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (g) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 3061.
15. For applications of the asymmetric oxazoline-mediated Ullmann coupling, see: (a) Meyers, A. I.; Willemsen, J. J. Tetrahedron 1998, 54, 10493. (b) Meyers, A. I.; Willemsen, J. J. J. Chem. Soc., Chem. Commun. 1997, 1573. Meyers, A. I.; Price, A. J. Org. Chem. 1998, 63, 412. (d) Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869. (e) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (f) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (g) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 3061.
16. For applications of the asymmetric oxazoline-mediated Ullmann coupling, see: (a) Meyers, A. I.; Willemsen, J. J. Tetrahedron 1998, 54, 10493. (b) Meyers, A. I.; Willemsen, J. J. J. Chem. Soc., Chem. Commun. 1997, 1573. Meyers, A. I.; Price, A. J. Org. Chem. 1998, 63, 412. (d) Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869. (e) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (f) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (g) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 3061.
17. For applications of the asymmetric oxazoline-mediated Ullmann coupling, see: (a) Meyers, A. I.; Willemsen, J. J. Tetrahedron 1998, 54, 10493. (b) Meyers, A. I.; Willemsen, J. J. J. Chem. Soc., Chem. Commun. 1997, 1573. Meyers, A. I.; Price, A. J. Org. Chem. 1998, 63, 412. (d) Meyers, A. I.; McKennon, M. J. Tetrahedron Lett. 1995, 36, 5869. (e) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 3259. (f) Nelson, T. D.; Meyers, A. I. J. Org. Chem. 1994, 59, 2655. (g) Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 3061.
18. For a review of the use of chiral oxazolines in synthesis, see: Meyers, A. I. J. Heterocycl. Chem. 1998, 35, 991 and references therein.
19. For general reviews on the Ullmann reaction, see: (a) Fanta, P. E. Synthesis 1974, 9. (b) Fanta, P. E. Chem. Rev. 1964, 64, 613. Fanta, P. E. Chem. Rev. 1946, 38, 139.
20. For general reviews on the Ullmann reaction, see: (a) Fanta, P. E. Synthesis 1974, 9. (b) Fanta, P. E. Chem. Rev. 1964, 64, 613. Fanta, P. E. Chem. Rev. 1946, 38, 139.
21. For general reviews on the Ullmann reaction, see: (a) Fanta, P. E. Synthesis 1974, 9. (b) Fanta, P. E. Chem. Rev. 1964, 64, 613. Fanta, P. E. Chem. Rev. 1946, 38, 139.
22. (a) Bringmann, G.; Pabst, T.; Busemann, S.; Peters, K.; Peters, E.-M. Tetrahedron 1998, 54, 1425.
23. (b) Bringmann, G.; Pabst, T.; Rycroft, D. S.; Connolly, J. D. Tetrahedron Lett. 1999, 40, 483.
24. 10b
25. Aldrich Chemicals, 1998-1999.
26. (a) Blicke, F. F. Org. React. 1942, 1, 303.
27. (b) Bruson, H. A.; Macmullen, C. W. J. Am. Chem. Soc. 1941, 65, 270.
28. (c) Mannich, C.; Ritsert, K. Arch. Pharm. (Weinheim, Ger.) 1926, 264, 164.
29. (d) Mannich, C.; Ball, G. Arch. Pharm. (Weinheim, Ger.) 1926, 264, 65.
30. McKillop, A.; Fiaud, J.-C.; Hug, R. P. Tetrahedron 1974, 30, 1379.
31. 1H NMR integration.
32. Pfau, M.; Revial, G.; Guingant, A.; d'Angelo, J. J. Am. Chem. Soc. 1985, 107, 273.
33. 3. equation presented
34. (a) Meyers, A. I.; Lefker, B. A. J. Org. Chem. 1986, 51, 1541.
35. (b) Wenkert, E.; Buckwater, B. L.; Craviero, A. A.; Sanchez, E. L.; Sathe, S. S. J. Am. Chem. Soc. 1978, 100, 1267.
36. (a) Todd, D. Org. React. 1948, 4, 378.
37. (b) Wolff, L. Liebigs Ann. Chem. 1912, 394, 86.
38. (c) Kishner, N. J. Russ. Phys. Chem. Soc. 1911, 43, 582.
39. (a) Barton, D. H. R.; Ives, D. A. J.; Thomas, B. R. J. Chem. Soc. 1955, 2056.
40. (b) Barton, D. H. R.; Ives, D. A. J.; Thomas, B. R. J. Chem. Soc. 1954, 903.
41. (c) Huang-Minlon, J. Am. Chem. Soc. 1949, 71, 3301.
42. Lajoie, G.; Lépine, F.; Maziak, L.; Belleau, B. Tetrahedron Lett. 1983, 24, 3815.
43. (a) Scheibye, S.; Shabuna, R.; Lawesson, S.-O.; Romming, C. Tetrahedron 1982, 38, 993.
44. (b) Karakasa, T.; Motoki, S. J. Org. Chem. 1978, 63, 4147 and references therein.
45. Onopchenko, A.; Schulz, J. G. D.; Seekircher, R. J. Org. Chem. 1972, 37, 1414.
46. Frump, J. A. Chem. Rev. 1971, 71, 483.
47. 7 It was not until completion of the syntheses of 2 and 3 that the assignment was verified.
48. (a) Hirsch, J. A. Top. Stereochem. 1967, 1, 199.
49. (b) Eliel, E. L., Manoharan, M. J. Org. Chem. 1981, 46, 1959.
50. (c) Allinger, N.; Freiberg, L. J. Org. Chem. 1966, 31, 804.
51. Fuson, R. C.; Cleveland, E. A. Organic Syntheses; Wiley: New York, 1955; Vol. III, p 339.