Enantioselective synthesis of 1,2-acetonide of (2S,3R)-3-N-Boc-3-amino-4-phenyl-1,2-butanediol

Tetrahedron Asymmetry

Volumn 7, Issue 4, 1996, Pages 1181-1188

  Remuzon, Philippe ^a   Dussy, Christian ^a   Jacquet, Jean Pierre ^a   Roty, Pascale ^a   Bouzard, Daniel ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANEDIOL DERIVATIVE; ANTIVIRUS AGENT; PROTEINASE INHIBITOR;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029996372     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00124-3     Document Type: Article

References (14)

1. For a recent review of anti-HIV drugs, see: De Clerq, E. J. Med. Chem., 1995, 38, 2491.
2. Barrish, J.C.; Gordon, E.; Alam, M.; Lin, P-F.; Bisacchi, G.S.; Chen, P.; Cheng, P.T.W.; Fritz, A.W.; Greytok, J.A.; Hermsmeier, M.A.; Humphreys, W.G.; Lis, K.A.; Marella, M.A.; Merchant, Z.; Mitt, T.; Morrison, R.A.; Obermeier, M. T.; Pluscec, J.; Skoog, M.; Slusarchyk, W.A.; Spergel, S.H.; Stevenson, J.M.; Sun, C-q.; Sundeen, J.E.; Taunk, P.; Tino, J.A.; Warrack, B.M.; Colonno, R.J.; Zahler, R. J. Med. Chem., 1994, 37, 1758.
3. a) Rich, D.H.; Vara Prasad J.V.N.; Sun, C-Q.; Green, J.; Mueller, R.; Houseman, K.; MacKenzie, D.; Malkovsky, M. J. Med. Chem., 1992, 35, 3803.
4. b) Ng, J.S.; Przybyla, C.A.; Liu, C.; Yen, J.C.; Muellner, F.W.; Weyker, C.L. Tetrahedron 1995, 51, 6397.
5. Luche, J.L.; Rodriguez-Hahn, L.; Crabbe, P. J. Chem. Soc., Chem. Commun., 1978, 14, 601.
6. It is likely that dehydrohalogenation first took place to give an intermediate similar to 17, followed by a Michael addition of the acetoxy anion to provide racemic 7. An intermediate analogous to 17 has already been described, see Gordon, E.W.; Pluscec, J.; Delaney, N.G.; Natarajan, S.; Sundeen, J. Tetrahedron Lett., 1984, 25, 3277. formula presented 17
7. Baker W.R.; Condon, S.L. J. Org. Chem., 1993, 58, 3277.
8. Claremon, D.A.; Lumma, P.K.; Phillips, B.T. J. Am. Chem. Soc., 1986, 108, 8265.
9. (R)-Isopropylidene glyceraldehyde 9 is now commercially available from Chemi (Milano, Italy).
10. Schmid, C.R.; Bryant, J.D.; Dowlatzedah, M.; Phillips, J.L.; Prather, D.E.; Schantz, R.D.; Sear, N.L.; Vianco, C.S. J. Org. Chem., 1990, 56, 4056.
11. Denmark, S.E.; Nicaise, O.; Edwards, J.P. J. Org. Chem., 1990, 55, 6219.
12. Hanson, G.J.; Lindberg, T. J. Org. Chem., 1985, 50, 5399.
13. 11
14. Jungheim L.N., Shepherd, T.A., Baxter, A.J., Burgess, J., Hatch, S.D., Lubbhusen, P., Wiskerchen, MA., Muesing, M. A. J. Med. Chem. 1996, 39, 96.