Total synthesis of the Annonaceous acetogenin (+)-asimicin. Development of a new bidirectional strategy

Journal of Organic Chemistry

Volumn 62, Issue 17, 1997, Pages 5989-5995

  Marshall, James A ^a   Hinkle, Kevin W ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOGENIN; ASIMICIN; NATURAL PRODUCT; PLANT EXTRACT; UNCLASSIFIED DRUG;

ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR MODEL; PLANT; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0030821863     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970423s     Document Type: Article

References (28)

1. (a) Zeng, L.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 275.
2. (b) Zhao, G. X.; Chao, J.-F.; Zeng, L.; Rieser, M. J.; McLaughlin, J. L. Bioorg. Med. Chem. 1996, 4, 25.
3. (c) For a previous synthesis, see: Hoye, T. R.; Tan, L. Tetrahedron Lett. 1995, 36, 1981.
4. (a) Figadere, B. Acc. Chem. Res. 1995, 28, 359.
5. (b) Koert, U. Synthesis 1995, 115.
6. Hoye, T. R.; Ye, Z. J. Am. Chem. Soc. 1996, 118, 1801 and references therein.
7. 2 symmetric diastereomers of IV have been reported. Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1996, 61, 4247.
8. Marshall, J. A.; Welmaker, G. S.; Gung, B. W. J. Am. Chem. Soc. 1991, 113, 647.
9. 2TMS. Lipshutz, B.; Miller, T. A. Tetrahedron Lett. 1989, 30, 7149.
10. McDougal, P. M.; Rico, J. G.; Oh, Y. I.; Condon, D. B. J. Org. Chem. 1986, 51, 3388.
11. The program Macromodel V4.5 was employed for these calculations. Global minimum multiple conformer searching was achieved with the Monte Carlo subroutine in BATCHMIN through a 2000-step iteration. The ten lowest energy conformers, covering an energy range of 22 kJ, were examined. Of these, conformers 1 (86.4 kJ), 2 (90.3 kJ), 4(97.1 kJ), 7 (102.5 kJ), and 10 (108.4 kJ) showed hydrogen bonding between the core THF unit and one of the terminal OH groups. Conformer 5 (99.2 kJ) showed no H bonding, and conformers 8 (103.5 kJ) and 9 (103.9 kJ) showed H bonding between the two terminal OH groups.
12. Corey, E. J.; Pyne, S. G.; Su, W. Tetrahedron Lett. 1983, 24, 4883.
13. Marshall, J. A.; Wolf, M. A. J. Org. Chem. 1996, 61, 3238.
14. Prepared from the TBS ether of (R)-lactaldehyde. Marshall, J. A.; Xie, S. J. Org. Chem. 1995, 60, 7230.
15. Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1991, 56, 3211.
16. Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323.
17. For a review, see: Marshall, J. A. Chemtracts: Organic Chemistry 1996, 280.
18. Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095.
19. Marshall, J. A.; Wolf, M. A.; Perkins, J. J. Org. Chem. 1995, 60, 5556.
20. Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovec, J. M.; Baldwin, J. J.; Christy, E.; Ponticello, G. S.; Varga, S. L.; Springer, J. D. J. Org. Chem. 1986, 51, 2370.
21. This procedure was developed by Clark A. Sehon in our laboratory. An earlier version can be found in ref 9.
22. Marshall, J. A.; Sehon, C. A. J. Org. Chem. 1995, 60, 5966.
23. This procedure was first employed by Kevin Gill of our laboratory.
24. Lipshutz, B. H.; Wilhelm, R. S.; Kozlowski, J. A.; Parker, D. J. Org. Chem. 1984, 49, 3928.
25. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
26. Kolb, H. C.; Sharpless, K. B. Tetrahedron Lett. 1992, 48, 10515.
27. Cf. Knapp, S.; Lal, G. S.; Sahai, D. J. Org. Chem. 1986, 51, 380.
28. Marshall J. A.; Chen, M. J. Org. Chem. 1997, 62, 5996.