Chemoenzymatic studies: From cycloheptatriene to the core of zaragozic acids

Tetrahedron Letters

Volumn 38, Issue 7, 1997, Pages 1117-1120

  Xu, Yanping ^a   Johnson, Carl R ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO[3.2.1]OCTANE DERIVATIVE; SQUALENE SYNTHASE INHIBITOR; TRIACYLGLYCEROL LIPASE; ZARAGOZIC ACID A;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENZYME ACTIVITY; REACTION ANALYSIS; STEREOCHEMISTRY;

CANDIDA ANTARCTICA;

EID: 0031575571     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00086-5     Document Type: Article

References (18)

1. 1 Dufresne, C.; Wilson, K. E.; Zink, D. L.; Smith, J.; Bergstrom, J. D.; Kurtz, M. M.; Rew, D.; Nallin, M.; Jenkins, R.; Bartizal, K.; Trainor, C.; Bills, G.; Meinz, M.; Huang, L.; Onishi, J.; Milligan, J. A.; Mojena, M.; Pelaez, F. Tetrahedron 1992, 47, 10221; Santini, C.; Ball, R. G.; Berger, G. D. J. Org. Chem. 1994, 59, 2261 and references cited therein.
2. 1 Dufresne, C.; Wilson, K. E.; Zink, D. L.; Smith, J.; Bergstrom, J. D.; Kurtz, M. M.; Rew, D.; Nallin, M.; Jenkins, R.; Bartizal, K.; Trainor, C.; Bills, G.; Meinz, M.; Huang, L.; Onishi, J.; Milligan, J. A.; Mojena, M.; Pelaez, F. Tetrahedron 1992, 47, 10221; Santini, C.; Ball, R. G.; Berger, G. D. J. Org. Chem. 1994, 59, 2261 and references cited therein.
3. 2 Dawson, H.; Farthing, J. E.; Marshall, P. S.; Middleton, R. F.; O'Neill, M. J.; Shuttleworth, A.; Stylli, C.; Tait, R. M.; Taylor, P. M.; Wildman, H. G.; Buss, A. D.; Langley, D.; Hayes, M. V.; J. Antibiot. 1992, 45, 639; Sidebottom, P. J.; Highcock, R. M.; Lane, S. J.; Procopiou, P. A.; Watson, N. S. J. Antibiot., 1992, 45, 648. See also Blows, W. M.; Foster, G.; Lane, S. J.; Noble, D.; Piercy, J. E.; Sidebottom, P. J.; Webb, G. J. Antibiot. 1994, 47, 740.
4. 2 Dawson, H.; Farthing, J. E.; Marshall, P. S.; Middleton, R. F.; O'Neill, M. J.; Shuttleworth, A.; Stylli, C.; Tait, R. M.; Taylor, P. M.; Wildman, H. G.; Buss, A. D.; Langley, D.; Hayes, M. V.; J. Antibiot. 1992, 45, 639; Sidebottom, P. J.; Highcock, R. M.; Lane, S. J.; Procopiou, P. A.; Watson, N. S. J. Antibiot., 1992, 45, 648. See also Blows, W. M.; Foster, G.; Lane, S. J.; Noble, D.; Piercy, J. E.; Sidebottom, P. J.; Webb, G. J. Antibiot. 1994, 47, 740.
5. 2 Dawson, H.; Farthing, J. E.; Marshall, P. S.; Middleton, R. F.; O'Neill, M. J.; Shuttleworth, A.; Stylli, C.; Tait, R. M.; Taylor, P. M.; Wildman, H. G.; Buss, A. D.; Langley, D.; Hayes, M. V.; J. Antibiot. 1992, 45, 639; Sidebottom, P. J.; Highcock, R. M.; Lane, S. J.; Procopiou, P. A.; Watson, N. S. J. Antibiot., 1992, 45, 648. See also Blows, W. M.; Foster, G.; Lane, S. J.; Noble, D.; Piercy, J. E.; Sidebottom, P. J.; Webb, G. J. Antibiot. 1994, 47, 740.
6. 3 For a review of the chemistry and biology of the zaragozic acids (squalestatins) see Nadin; A.; Nicolaou, K. C. Angew. Chem. Int. Ed. Engl. 1996, 35, 1622; For a review of published total syntheses see Koert; U. Angew. Chem. Intl. Ed. Engl. 1995, 34, 773.
7. 3 For a review of the chemistry and biology of the zaragozic acids (squalestatins) see Nadin; A.; Nicolaou, K. C. Angew. Chem. Int. Ed. Engl. 1996, 35, 1622; For a review of published total syntheses see Koert; U. Angew. Chem. Intl. Ed. Engl. 1995, 34, 773.
8. 4 Carreira, E. M.; Du Bois, J. J. Am. Chem. Soc. 1994, 116, 10825; 1995, 117, 8106.
9. 4 Carreira, E. M.; Du Bois, J. J. Am. Chem. Soc. 1994, 116, 10825; 1995, 117, 8106.
10. 5 Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; Yue, E. W.; La Greca, S. Angew. Chem. Int. Ed. Engl. 1994, 33, 2190; Nicolaou, K. C.; Yue, E. W.; La Greca, S.; Nadin, A.; Yang Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; Riccardis, F. D. Chem. Eur. J. 1995, 1, 467.
11. 5 Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; Yue, E. W.; La Greca, S. Angew. Chem. Int. Ed. Engl. 1994, 33, 2190; Nicolaou, K. C.; Yue, E. W.; La Greca, S.; Nadin, A.; Yang Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; Riccardis, F. D. Chem. Eur. J. 1995, 1, 467.
12. 6 Evans, D. A.; Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M. J. J. Am. Chem. Soc. 1994, 116, 12111.
13. 7 For an abstract describing a relay synthesis see: Heathcock, C. H.; Caron, S.; Stoermer, D. 209th National Meeting of the American Chemical Society: Anaheim, CA, 1995, ORGN 170.
14. 8 For a recent synthesis of the core of zaragozic acids see Paterson, I.; Fessner, K.; Finlay, M. R. V.; Jacobs, M. F. Tetrahedron Lett. 1996, 37, 8803-8806; for references to additional model studies see ref. 3 and 4.
15. 9 For example see Johnson, C. R.; Golebiowski, A.; Steensma, D. H. J. Am. Chem. Soc. 1992, 114, 9414.
16. 10 Scialdone, M. A.; Johnson, C.R. Tetrahedron Lett. 1995, 36, 43.
17. 11 Rubottom, G. R.; Vazquez, M. A.; Pelegrina, D. R. Tetrahedron Lett. 1974, 75, 4319.
18. 12 Pilcher, A. S.; DeShong, P. J. Org. Chem. 1993, 58, 5130.