Enzymatic resolution of thiazole-containing vinyl carbinols. Synthesis of the C12-C21 fragment of the epothilones

Tetrahedron Letters

Volumn 41, Issue 12, 2000, Pages 1863-1866

  Zhu, Bin ^a   Panek, James S ^a  

^a Boston University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; EPOTHILONE DERIVATIVE; MACROLIDE; UNCLASSIFIED DRUG;

ARTICLE; ENANTIOMER; SYNTHESIS;

EID: 0034681737     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00061-7     Document Type: Article

References (16)

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3. (a) Harris, C. R.; Kuduk, S. D.; Balog, A.; Savin, K.; Glunz, P. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 7050-7062.
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7. (e) White, J. D.; Sundermann, K. F.; Carter, R. G. Organic Lett. 1999, 1, 1431-1434.
8. (a) Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Roschangar, F.; Sarabia, F.; Ninkovic, S.; Yang, Z.; Trujillo, J. I. J. Am. Chem. Soc. 1997, 119, 7960-7973.
9. (b) Meng, D.; Bertinato, P.; Balog, A.; Su, D. S.; Kamenecka, T.; Sorensen, E. J.; Danishefsky, S. J. J. Am. Chem. Soc. 1997, 119, 10073-10092.
10. (c) Schinzer, D.; Limberg, A.; Bauer, A.; Bohm, O. M.; Cordes, M. Angew. Chem.; Int. Ed. Engl. 1997, 36, 523-524.
11. (d) Ref. 2c.
12. Synthesis of C12-C21 fragment utilizing aldolase: (a) Machajewski, T. D.; Wong, C. H. Synthesis 1999, 1469-1472.
13. (b) Sinha, S. C.; Sun, J.; Miller, G.; Barbas III, C. F.; Lerner, R. A. Organic Lett. 1999, 1, 1623-1626.
14. D of the obtained (S)-3 and (S)-4 with the reported data. The enzymatic stereoselectivity factor E was calculated according to the method of Kagan. See: Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249-330.
15. Corey, E. J.; Cashman, J. R.; Eckrich, T. M.; Corey, D. R. J. Am. Chem. Soc. 1985, 107, 713-715.
16. 1H NMR, measuring the integration of the methine proton adjacent to the hydroxyl group and the methine proton adjacent to the acetate group. When the ratio of acetate and alcohol in the reaction mixture reached ca. 1:1 (72 h), the insoluble enzyme was removed by filtration, and washed with ether (200 mL). Concentration of the filtrate in vacuo and silica gel flash chromatography afforded the acetate (R)-11 (15% ethyl acetate in hexane, 2.1 g, 48%, light yellow oil) and the unreacted alcohol (S)-10 (35% acetate in hexane, 1.73 g, 48%, light yellow oil).