Enzymatic single aldol reactions of remote dialdehydes

Tetrahedron Asymmetry

Volumn 8, Issue 9, 1997, Pages 1507-1509

  Kim, Mahn Joo ^a   Lim, In Taek ^a   Kim, Hee Jeong ^a   Wong, Chi Huey ^b  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; FRUCTOSE BISPHOSPHATE ALDOLASE;

ANIMAL TISSUE; ARTICLE; CARBOHYDRATE SYNTHESIS; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME ACTIVITY; IN VITRO STUDY; METHODOLOGY; MUSCLE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; RABBIT; REACTION ANALYSIS; STEREOCHEMISTRY; THIN LAYER CHROMATOGRAPHY;

EID: 0030992556     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00139-0     Document Type: Article

References (11)

1. Toone, E. J.; Simon, E. S.; Bednarski, M. D.; Whitesides, G. M. Tetrahedron 1989, 45, 5365. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994; Chapter 4. Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem. Int. Ed. Engl. 1995, 34, 412.
2. Toone, E. J.; Simon, E. S.; Bednarski, M. D.; Whitesides, G. M. Tetrahedron 1989, 45, 5365. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994; Chapter 4. Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem. Int. Ed. Engl. 1995, 34, 412.
3. Toone, E. J.; Simon, E. S.; Bednarski, M. D.; Whitesides, G. M. Tetrahedron 1989, 45, 5365. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994; Chapter 4. Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem. Int. Ed. Engl. 1995, 34, 412.
4. Henerson, I.; Laslo, K.; Wong, C.-H. Tetrahedron Lett. 1994, 35, 359. Henderson, I.; Sharpless, K. B.; Wong, C.-H. J. Am. Chem. Soc. 1994, 116, 558. Gijsen, H. J. M.; Wong, C.-H. J. Am. Chem. Soc. 1995, 117, 2947 and 7585.
5. Henerson, I.; Laslo, K.; Wong, C.-H. Tetrahedron Lett. 1994, 35, 359. Henderson, I.; Sharpless, K. B.; Wong, C.-H. J. Am. Chem. Soc. 1994, 116, 558. Gijsen, H. J. M.; Wong, C.-H. J. Am. Chem. Soc. 1995, 117, 2947 and 7585.
6. Henerson, I.; Laslo, K.; Wong, C.-H. Tetrahedron Lett. 1994, 35, 359. Henderson, I.; Sharpless, K. B.; Wong, C.-H. J. Am. Chem. Soc. 1994, 116, 558. Gijsen, H. J. M.; Wong, C.-H. J. Am. Chem. Soc. 1995, 117, 2947 and 7585.
7. Eyrisch, O.; Fessner, W.-D. Angew. Chem. Int. Ed. Engl. 1995, 34, 1639.
8. For the RAMA-catalyzed aldol condensation of half-protected dialdehydes, see Borysenko, C. W.; Spaltenstein, A.; Straub, J. A.; Whitesides, G. M. J. Am. Chem. Soc. 1989, 111, 9275.
9. For the synthesis of stereoisomeric 1c and 1d (R,R-, S,S, and meso-), see Kim, M.-J.; Lee, I. S. J. Org. Chem. 1993, 23, 6483.
10. 6 (M+H): 295.2121. Found: 295.2106.
11. 7 (M+H): 293.1601. Found: 293.1603.