Gram-scale synthesis of (+)-discodermolide

Organic Letters

Volumn 1, Issue 11, 1999, Pages 1823-1826

  Smith III, Amos B ^a   Kaufman, Michael D ^a   Beauchamp, Thomas J ^a   LaMarche, Matthew J ^a   Arimoto, Hirokazu ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; ANTINEOPLASTIC AGENT; CARBAMIC ACID DERIVATIVE; DISCODERMOLIDE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; LACTONE; PYRONE DERIVATIVE;

ANIMAL; ARTICLE; CHEMISTRY; SPONGE (PORIFERA); STEREOISOMERISM; SYNTHESIS;

ALKANES; ANIMALS; ANTINEOPLASTIC AGENTS; CARBAMATES; INDICATORS AND REAGENTS; LACTONES; PORIFERA; PYRONES; STEREOISOMERISM;

EID: 0033518052     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9910870     Document Type: Article

References (26)

1. Gunasekera, S. P.; Gunasekera, M.; Longley, R. E.; Schulte, G. K. J. Org. Chem. 1990, 55, 4912; (correction) 1991, 56, 1346.
2. (a) Hung, D. T.; Chen, J.; Schreiber, S. L. Chem. Biol. 1996, 3, 287.
3. (b) ter Haar, E.; Kowalski, R. J.; Hamel, E.; Lin, C. M.; Longley, R. E.; Gunasekera, S. P.; Rosenkranz, H. S.; Day, B. W. Biochemistry 1996, 35, 243.
4. Schiff, P. B.; Frant, J.; Horwitz, S. B. Nature 1979, 277, 665.
5. Kowalski, R. J.; Giannakakou, P.; Gunasekera, S. P.; Longley, R. E.; Day, B. W.; Hamel, E. Mol. Pharmacol. 1997, 52, 613.
6. Total syntheses of 1 and ent-1 to date: (a) Nerenberg, J. B.; Hung, D. T.; Somers, P. K.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 12621.
7. (b) Smith, A. B., III.; Qiu, Y.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 1995, 117, 12011.
8. (c) Harried, S. S.; Yang, G.; Strawn, M. A.; Myles, D. C. J. Org. Chem. 1997, 62, 6098.
9. (d) Marshall, J. A.; Johns, B. A. J. Org. Chem. 1998, 63, 7885.
10. Mancuso, A. J.; Swern, D. Synthesis 1981, 165.
11. Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 77.
12. Walkup, R. D.; Kaḣl, J. D.; Kane, R. R. J. Org. Chem. 1998, 63, 9113.
13. 13C NMR spectra, as well as appropriate ion identification by HRMS.
14. Parikh, J. R.; Doering, W. von E. J. Am. Chem. Soc. 1967, 89, 5505.
15. Paterson, I. Tetrahedron Lett. 1979, 1519.
16. Negishi, E.; Valente, L. F.; Kobayashi, M. J. Am. Chem. Soc. 1980, 102, 3298.
17. Takano, S.; Akiyama, M.; Sato, S.; Ogasawara, K. Chem. Lett. 1983, 1593.
18. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
19. (a) Ikeda, Y.; Ukai, J.; Ikeda, N.; Yamamoto, H. Tetrahedron 1987, 43, 723.
20. (b) This protocol was first used in synthetic studies toward 1 by Heathcock and co-workers. See: Clark, D. L.; Heathcock, C. H. J. Org. Chem. 1993, 58, 5878.
21. Compounds listed without an optical rotation sign are a mixture of E/Z diene isomers; the major isomer is that depicted.
22. Boeckman, R. K., Jr.; Potenza, J. C. Tetrahedron Lett. 1985, 26, 1411.
23. Dauben, W. G.; Gerdes, J. M.; Bunce, R. A. J. Org. Chem. 1984, 49, 4293.
24. Qiu, Y. Ph.D. Dissertation, University of Pennsylvania, Philadelphia, PA. 1997.
25. The E isomer can adopt the S-cis conformation needed to undergo cycloaddition with DDQ, whereas the Z isomer is prohibited from adopting the requisite S-cis conformation due to significant steric interaction between the C(24) vinyl and C(20) methine protons.
26. Kocovsky, P. Tetrahedron Lett. 1986, 27, 5521.