Dianion equivalents corresponding to the polypropionate domain of epothilone B

Tetrahedron Letters

Volumn 40, Issue 12, 1999, Pages 2263-2266

  Harris, Christina R ^a   Kuduk, Scott D ^a   Savin, Ken ^c   Balog, Aaron ^d   Danishefsky, Samuel J ^a,b  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b Och Spine at New York Presbyterian Hospitals   (United States)

^c ELI LILLY AND COMPANY   (United States)

^d BRISTOL MYERS SQUIBB   (United States)

Author keywords

Aldol; Epothilone B; Methyl enol ether; Polypropionate

Indexed keywords

EPOTHILONE B;

ARTICLE; CHEMICAL ANALYSIS; CYTOTOXICITY; DRUG POTENCY; DRUG SYNTHESIS; MAXIMUM ALLOWABLE CONCENTRATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033583117     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00221-X     Document Type: Article

References (13)

1. 1 a.) Balog A.; Meng, D.; Kamenecka, T.; Bertinato, P.; Su, D.-S.; Sorensen, E.; Danishefsky, S. J. Angew Chem, Int Ed Engl 1996, 35, 2801
2. b.) Su, D.-S.; Meng, D.; Bertinato, P.; Balog, A.; Sorenson, E. J.; Danishefsky, S. J. Angew Chem, Int Ed Engl 1997, 36, 775.
3. c.) Meng, D.; Bertinato, P.; Balog, A.; Su, D.-S.; Kamenecka, T.; Sorensen, E.; Danishefsky, S. J. J. Am. Chem. Soc. 1997, 119, 10073.
4. 2 For other total syntheses see: a.) Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z.. Angew Chem, Int Ed Engl 1996, 35, 2399.
5. b.) Schinzer, D.; Limberg, A.; Bauer, A.; Bohm, O. M. Chem. Eur. J. 1996, 2, 1477.
6. c.) May, S. A.; Grieco, P. A. J. Chem. Soc., Chem. Comm. 1998, 1597.
7. d.) For a recent review of the epothilones see, Nicolaou, K. C.; Roschangar, F.; Vourloumis, D. Angew Chem, Int Ed Engl 1998, 37, 2014.
8. 3 Chou, T.-C.; Zhang, X.-G.; Harris, C. R.; Kuduk, S. D.; Balog, A.; Savin, K.; Danishefsky, S. J. Proc.Nat. Acad. Sci. 1998, in press.
9. 1H NMR spectrum of the major diastereomer with a compound of known stereochemistry that had been independently synthesized.
10. 5 Balog, A; Harris, C.; Savin, K. Angew Chem Int Ed Engl, 1998, 2675-2678.
11. 6 A detailed study of the source of this exceptional relative facial selectivity observed with α-methyl aldehydes is reported in the following article.
12. 3): δ 5.18 (s, 1H), 3.88 (s, 3H), 2.45 (q, J = 7.33 Hz, 2H), 1.48 (s, 9H), 1.25 (s, 6H), 1.02 (t, J = 7.21 Hz, 3H).
13. 3): δ 5.76 (m, 1H), 5.19 (s, 1H), 5.06 (m, 2H). 1.48 (s, 3H), 3.41 (m, 1H), 3.17 (m, 1H), 3.12 (m, 1H), 2.11 (m, 1H), 1.86 (m, 1H), 1.63 (m, 1H), 1.48 (s, 9H), 1.28 (s, 3H), 1.27 (s, 3H), 1.07 (d, J = 6.91 Hz, 3H), 0.99 (d, J = 6.04 Hz, 3H).