Highly diastereo- and enantioselective catalytic synthesis of the bis-tetrahydrofuran alcohol of Brecanavir and Darunavir

Tetrahedron Asymmetry

Volumn 19, Issue 17, 2008, Pages 2015-2019

  Black, David M ^a   Davis, Roman ^a   Doan, Brian D ^a   Lovelace, Tom C ^a   Millar, Alan ^a   Toczko, Jennifer F ^a   Xie, Shiping ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

(BENZYLOXY)ACETALDEHYDE; 3 [2 (BENZYLOXY) 1 HYDROXYETHYL]DIHYDROFURAN 2(3H) ONE; ACETAL DERIVATIVE; ACETALDEHYDE; ALCOHOL DERIVATIVE; AMPRENAVIR; ATAZANAVIR; BISTETRAHYDROFURAN ALCOHOL; BRECANAVIR; DARUNAVIR; INDINAVIR; LACTIC ACID 2 NAPHTHYL ESTER; LACTONE ALCOHOL DERIVATIVE; NELFINAVIR; PALLADIUM; PROTEINASE INHIBITOR; RITONAVIR; SAQUINAVIR; SILYL KETENE ACETAL; TETRAHYDROFURAN; TETRAHYDROFURO[2,3 B]FURAN 3(2H) ONE; TIPRANAVIR; TMC 114 2; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; CONTROLLED STUDY; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; EPIMER; HIGHLY ACTIVE ANTIRETROVIRAL THERAPY; HYDROGENOLYSIS; IN SITU CYCLIZATION; MUKAIYAMA REACTION; NONHUMAN; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION KINETICS; STEREOCHEMISTRY;

EID: 51449107593     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.07.037     Document Type: Article

References (35)

1. For recent reviews, see:. Ghosh A.K., Chapsal B.D., Weber I.T., and Mitsuya H. Acc. Chem. Res. 41 (2008) 78
2. Ghosh A.K., Sridhar P.R., Kumaragurubaran N., Koh Y., Weber I.T., and Mitsuya H. ChemMedChem 1 (2006) 939
3. Hanlon M.H., Porter D.J.T., Furfine E.S., Spaltenstein A., Carter H.L., Danger D., Shu A.Y.L., Kaldor I.W., Miller J.F., and Samano V.A. Biochemistry 43 (2004) 14500
4. Miller J.F., Andrews C.W., Brieger M., Furfine E.S., Hale M.R., Hanlon M.H., Hazen R.J., Kaldor I., McLean E.W., Reynolds D., Sammond D.M., Spaltenstein A., Tung R., Turner E.M., Xu R.X., and Sherrill R.G. Bioorg. Med. Chem. Lett. 16 (2006) 1788
5. Ghosh A.K., Shin D.W., Swanson L., Krishnan K., Cho H., Hussain K.A., Walters D.E., Holland L., and Buthod J. Farmaco 56 (2001) 29
6. Ghosh A.K., Kincaid J.F., Cho W., Walters D.E., Krishnan K., Hussain K.A., Koo Y., Cho H., Rudall C., Holland L., and Buthod J. J. Bioorg. Med. Chem. Lett. 8 (1998) 687
7. Koh Y., Nakata H., Maeda K., Ogata H., Bilcer G., Devasamudram T., Kincaid J.F., Boross P., Wang Y.-F., Tie Y., Volarath P., Gaddis L., Harrison R.W., Weber I.T., Ghosh A.K., and Mitsuya H. Antimicrob. Agent Chemother. 47 (2003) 3123
8. Yoshimura K., Kato R., Kavlick M.F., Nguyen A., Maroun V., Maeda K., Hussain K.A., Ghosh A.K., Gulnik S.V., Erickson J.W., and Mitsuya H. J. Virol. 76 (2002) 1349
9. Ghosh A.K., Kincaid J.F., Cho W., Walters D.E., Krishnan K., Hussain K.A., Koo Y., Cho H., Rudall C., Holland L., and Buthod J. Bioorg. Med. Chem. Lett. 8 (1998) 687
10. Surleraux D.L.N.G., Tahri A., Verschueren W.G., Pille G.M.E., de Kock H.A., Jonckers T.H.M., Peeters A., De Meyer S., Azijn H., Pauwels R., de Bethune M.-P., King N.M., Prabu-Jeyabalan M., Schiffer C.A., and Wigerinck P.B.T.P. J. Med. Chem. 48 (2005) 1813
11. Quaedflieg P.J.L.M., Kesteleyn B.R.R., Wigerinck P.B.T.P., Goyvaerts N.M.F., Vijn R.J., Liebregts C.S.M., Kooistra J.H.M.H., and Cusan C. Org. Lett. 7 (2005) 5917
12. Ghosh A.K., Leshchenko S., and Noetzel M. J. Org. Chem. 69 (2004) 7822
13. Ghosh A.K., Kincaid J.F., Walters D.E., Chen Y., Chaudhuri N.C., Thompson W.J., Culberson C., Fitzgerald P.M.D., Lee H.Y., McKee S.P., Munson P.M., Duong T.T., Darke P.L., Zugay J.A., Schleif W.A., Axel M.G., Lin J., and Huff J.R. J. Med. Chem. 39 (1996) 3278
14. Ghosh A.K., and Chen Y. Tetrahedron Lett. 36 (1995) 505
15. Ghosh A.K., Thompson W.J., Fitzgerald P.M.D., Culberson J.C., Axel M.G., McKee S.P., Huff J.R., and Anderson P.S. J. Med. Chem. 37 (1994) 2506
16. Roberts, J. C.; Toczko, J. F. PCT/US2004/020353, WO 2005/000249 A2.
17. Uchiyama M., Hirai M., Nagata M., Katoh R., Ogawa R., and Ohta A. Tetrahedron Lett. 42 (2001) 4653
18. Ghosh A.K., Li J., and Perali R.S. Synthesis (2006) 3015
19. Yu R.H., Polniaszek R.P., Becker M.W., Cook C.M., and Yu L.H.L. Org. Process Res. Dev. 11 (2007) 972
20. Canoy W.L., Cooley B.E., Corona J.A., Lovelace T.C., Millar A., Weber A.M., Xie S., and Zhang Y. Org. Lett. 10 (2008) 1103
21. Oisaki K., Suto Y., Kanai M., and Shibasaki M. J. Am. Chem. Soc. 125 (2003) 5644
22. Widdowson D.A., Wiebecke G.H., and Williams D.J. Tetrahedron Lett. 23 (1982) 4285
23. Ruano J.L.G., Barros D., Maestro M.C., Slawin A.M.Z., and Page P.C.B. J. Org. Chem. 65 (2000) 6027
24. While we have not seen reports of highly stereoselective addition of γ-butyrolactone to glyoxylate esters, there are many reports on selective aldol addition of acyclic enolates to glyoxylate esters. For some examples, see. Evans D.A., Masse C.E., and Wu J. Org. Lett. 4 (2002) 3375
25. Evans D.A., MacMillan D.W.C., and Campos K.R. J. Am. Chem. Soc. 119 (1997) 10859
26. Maikami K., and Matsukawa S. J. Am. Chem. Soc. 116 (1994) 4077
27. Evans D.A., Murry J.A., and Kozlowski M.C. J. Am. Chem. Soc. 118 (1996) 5814
28. Evans D.A., Kozlowski M.C., Murry J.A., Burgey C.S., Campos K.R., Connell B.T., and Staples R.J. J. Am. Chem. Soc. 121 (1999) 669
29. Evans D.A., Zachary K., Sweeney T.R., and Jason S.T. J. Am. Chem. Soc. 123 (2001) 12095
30. Evans D.A., and Johnson J.S. J. Am. Chem. Soc. 120 (1998) 4895
31. Johnson J.S., and Evans D.A. Acc. Chem. Res. 33 (2000) 325
32. Zenk P.C., and Weley R.A. Synthesis (1984) 695
33. White J., and Hanciar P. J. Org. Chem. 65 (2000) 9129
34. Chiral GC conditions are as follows. Column: Astec Chiraldex Gamma Cyclodextrin trifluoroacetyl (G-TA) 20 m × 0.25 mm. Carrier gas: He @ 1 mL/min. Make-up gas: He @ 30 mL/min. Temperature: isothermal @ 140 °C. Detection: FID at 300 °C. Injection: 1 μL @ 250 °C. Split flow: 100 mL/min. Carrier + makeup flow: 31 mL/min. Run time: 15 min. Retention time (min): 7.47 for 3; 7.82 for ent-3; 9.16 for 6; 8.93 for ent-6.
35. Griffith W.P., and Ley S.V. Synthesis (1994) 639