Chiral polypropionate subunit by a chemoenzymatic approach

Tetrahedron Asymmetry

Volumn 9, Issue 15, 1998, Pages 2559-2561

  Bonini, C ^a   Chiummiento, L ^a   Funicello, M ^a   Marconi, L ^a   Righi, G ^b  

^a UNIVERSITY OF BASILICATA   (Italy)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

4 METHYL 3,5 DIOXOLAN 1,3,5,7 TETROL; PROPIONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DRUG STRUCTURE; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0032493773     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00256-0     Document Type: Article

References (21)

1. O'Hagan, D. Nat. Prod. Rep. 1995, 12, 1 and references cited therein.
2. Dutton, C. J.; Banks, B. J.; Cooper, C. B. Nat. Prod. Rep. 1995, 12, 165 and references cited therein.
3. See: (a) Heathcock, C. H. In Comprehensive Organic Synthesis, Trost, B. M., Fleming, I., Heathcock, C. H., Eds; Pergamon Press: Oxford, 1991; Vol. 2, pp. 181-238. (b) Kim, M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis, Trost, B. M., Fleming, I., Heathcock, C. H., Eds; Pergamon Press: Oxford, 1991; Vol. 2, pp. 239-275. (c) Paterson, I. Pure Appl. Chem. 1992, 64, 1821.
4. See: (a) Heathcock, C. H. In Comprehensive Organic Synthesis, Trost, B. M., Fleming, I., Heathcock, C. H., Eds; Pergamon Press: Oxford, 1991; Vol. 2, pp. 181-238. (b) Kim, M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis, Trost, B. M., Fleming, I., Heathcock, C. H., Eds; Pergamon Press: Oxford, 1991; Vol. 2, pp. 239-275. (c) Paterson, I. Pure Appl. Chem. 1992, 64, 1821.
5. See: (a) Heathcock, C. H. In Comprehensive Organic Synthesis, Trost, B. M., Fleming, I., Heathcock, C. H., Eds; Pergamon Press: Oxford, 1991; Vol. 2, pp. 181-238. (b) Kim, M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis, Trost, B. M., Fleming, I., Heathcock, C. H., Eds; Pergamon Press: Oxford, 1991; Vol. 2, pp. 239-275. (c) Paterson, I. Pure Appl. Chem. 1992, 64, 1821.
6. Nicholas, G. In Comprehensive Organic Synthesis, Trost, B. M., Fleming, I., Heathcock, C. H., Eds; Pergamon Press: Oxford, 1991; Vol. 8, pp. 1-24.
7. Domon, L.; Vogeleisen, F.; Uguen, D. Tetrahedron Lett. 1996, 37, 2773.
8. Chenevert, R.; Courchesne, G. Tetrahedron: Asymmetry 1995, 6, 2093.
9. (a) Bonini, C.; Racioppi, R.; Righi, G.; Viggiani, L. J. Org. Chem. 1993, 58, 802.
10. (b) Bonini, C.; Racioppi, R.; Righi, G.; Rossi, L.; Viggiani, L. Tetrahedron: Asymmetry 1993, 4, 793.
11. Bonini, C.; Giugliano, A.; Racioppi, R.; Righi, G. Tetrahedron Lett. 1996, 37, 2487.
12. 13C-NMR analysis of the corresponding acetonide derivatives.
13. PPL (Porcine Pancreatic Lipase) and PFL (Pseudomonas fluorescens Lipase) are commercially available from FLUKA.
14. Both the reactions were carried out, on a gram scale, in diethyl ether with a 0.06 M concentration of substrate, 0.6 M of vinylacetate and 30 U/mg of enzyme.
15. The reaction was carried out in phosphate buffer 0.2 M at pH=7 in 2 h.
16. 3 signals of the isopropylidene ring.
17. 3).
18. All new compounds exhibited satisfactory spectroscopic exact mass data.
19. The syn-syn prepared subunits can be found, i.e. in calyculin, a potent inhibitor of protein phosphonate (for structure and synthesis see Hamada, Y.; Yokokawa, F.; Kabeya, M.; Hatano, K.; Kurono, Y.; Shioiri, T. Tetrahedron 1996, 52, 8297, and references cited therein); in the immunosuppressant (-)-FK-506 (see for structure Tanaka, H.; Kuroda, A.; Marusawa, H.; Hatanaka, H.; Kino, T.; Goto, T.; Hashimoto, M.; Taga, T. J. Am. Chem. Soc. 1987, 111, 1157); and in conagenin, a new immunomodulator (Hatakeyama, S.; Fukuyama, H.; Mukugi, Y.; Irie, H. Tetrahedron Lett. 1996, 37, 4047).
20. The syn-syn prepared subunits can be found, i.e. in calyculin, a potent inhibitor of protein phosphonate (for structure and synthesis see Hamada, Y.; Yokokawa, F.; Kabeya, M.; Hatano, K.; Kurono, Y.; Shioiri, T. Tetrahedron 1996, 52, 8297, and references cited therein); in the immunosuppressant (-)-FK-506 (see for structure Tanaka, H.; Kuroda, A.; Marusawa, H.; Hatanaka, H.; Kino, T.; Goto, T.; Hashimoto, M.; Taga, T. J. Am. Chem. Soc. 1987, 111, 1157); and in conagenin, a new immunomodulator (Hatakeyama, S.; Fukuyama, H.; Mukugi, Y.; Irie, H. Tetrahedron Lett. 1996, 37, 4047).
21. The syn-syn prepared subunits can be found, i.e. in calyculin, a potent inhibitor of protein phosphonate (for structure and synthesis see Hamada, Y.; Yokokawa, F.; Kabeya, M.; Hatano, K.; Kurono, Y.; Shioiri, T. Tetrahedron 1996, 52, 8297, and references cited therein); in the immunosuppressant (-)-FK-506 (see for structure Tanaka, H.; Kuroda, A.; Marusawa, H.; Hatanaka, H.; Kino, T.; Goto, T.; Hashimoto, M.; Taga, T. J. Am. Chem. Soc. 1987, 111, 1157); and in conagenin, a new immunomodulator (Hatakeyama, S.; Fukuyama, H.; Mukugi, Y.; Irie, H. Tetrahedron Lett. 1996, 37, 4047).