Synthetic applications of the cyclic iminocarbonate rearrangement Enantioselective syntheses of chloramphenicol and 4-epi-cytoxazone

Tetrahedron Letters

Volumn 41, Issue 29, 2000, Pages 5553-5556

  Park, Jung Nam ^a   Ko, Soo Y ^a   Koh, Hun Y ^b  

^a Ewha Womans University   (South Korea)

^b Korea Institute of Science and Technology   (South Korea)

Author keywords

4 epi cytoxazone; Chloramphenicol; Cyclic iminocarbonate rearrangement; Enantioselective synthesis; Regioselection

Indexed keywords

4 EPI CYTOXAZONE; ACETONITRILE; AMINOALCOHOL; CARBONIC ACID; CHLORAMPHENICOL; CINNAMIC ACID DERIVATIVE; IMINE; METHANOL DERIVATIVE; SODIUM BOROHYDRIDE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; HYDROXYLATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0000862806     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00878-9     Document Type: Article

References (20)

1. (a) Enantioselective Synthesis of β-amino Acids; Ojima, I., Ed.; VCD Publishers: New York, 1996, and references cited therein.
2. (b) Cole, D. C. Tetrahedron 1994, 50, 9517.
3. (c) Juraristi, E.; Quintana, D.; Escalante, J. Aldrichim. Acta 1994, 27, 3.
4. (d) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 25, 117.
5. For a review, see: Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed. Catalytic asymmetric epoxidation of allylic alcohols. VCD Publishers: New York, 1993; pp. 103-158.
6. For a review, see: Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
7. For a review, see: O'Brien, P. Angew. Chem., Int. Ed. Engl. 1999, 38, 326.
8. cf. A reversal of regioselection in the AA process has been reported. See: (a) Tao, B.; Schlingloff, G.; Sharpless, K. B. Tetrahedron Lett. 1998, 39, 2507.
9. (b) Morgan, A. J.; Masse, C. E.; Panek, J. S. Org. Lett. 1999, 1, 1949.
10. The diastereocontrol is achieved in the AE-based strategy by using cis/trans-epoxy alcohol substrates; the regiocontrol requires a C-2/C-3 regioselective ring-opening of the epoxy alcohols with a nitrogen nucleophile.
11. In 2,3-syn-dihydroxy esters, the α-hydroxyl group is selectively converted to a leaving group (sulfonate), which allows an introduction of a nitrogen functionality there (at C-2). See Ref. 3 and: Fleming, P. R.; Sharpless, K. B. J. Org. Chem. 1991, 56, 2869.
12. anti-Diols, potentially more straightforward diol precursors for syn-amino alcohols, are not directly accessible via AD as (Z)-disubstituted alkenes are generally poor substrates in this process. cf. Ko, S. Y.; Malik, M.; Dickinson, A. F. J. Org. Chem. 1994, 59, 2570.
13. (a) Cho, G. Y.; Ko, S. Y. J. Org. Chem. 1999, 64, 8745.
14. (b) Cho, G. Y.; Park, J. N.; Ko, S. Y. Tetrahedron Lett. 2000, 41, 1789.
15. Lednicer, D. Strategies for Organic Drug Synthesis and Design; John Wiley & Sons, 1998.
16. The optical purity was determined using chiral HPLC (Pirkle or Chiralcel OD column).
17. (a) Kakeya, H.; Morishita, M.; Kobinata, K.; Osono, M.; Ishizuka, M.; Osada, H. J. Antibiot. 1998, 51, 1126.
18. (b) Kakeya, H.; Morishita, M.; Koshino, H.; Morita, T.-i.; Kobayashi, K.; Osada, H. J. Org. Chem. 1999, 64, 1052.
19. (c) Sakamoto, Y.; Shiraishi, A.; Seonhee, J.; Nakata, T. Tetrahedron Lett. 1999, 40, 4203.
20. (d) Miyata, O.; Asai, H.; Naito, T. Synlett 1999, 12, 1915.