Synthetic studies of the HIV-1 protease inhibitive didemnaketals: Stereocontrolled synthesis of an ester side chain

Tetrahedron Letters

Volumn 45, Issue 19, 2004, Pages 3713-3716

  Zhao, Xue Zhi ^a   Tu, Yong Qiang ^a   Peng, Lei ^a   Li, Xue Qiang ^a   Jia, Yan Xing ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

Ester side chain; Grob fragmentation reaction; HIV 1 protease; Intramolecular chiral inducement

Indexed keywords

ACETAL DERIVATIVE; ALLYL ALCOHOL; CARVONE; ESTER; PROTEINASE INHIBITOR;

ARTICLE; ASCIDIACEA; CHIRALITY; DIASTEREOISOMER; DRUG INHIBITION; DRUG SYNTHESIS; EPOXIDATION; FRAGMENTATION REACTION; MOLECULAR INTERACTION; STEREOCHEMISTRY;

ASCIDIA; DIDEMNUM; DIDEMNUM SP.; HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 1842839876     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.103     Document Type: Article

References (17)

1. Potts B.C.M., Faulker D.J. J. Am. Chem. Soc. 113:1991;6321.
2. Pika J., Faulkner D.J. Nat. Prod. Lett. 7:1995;291.
3. Salomon C.E., Williams D.H., Lobkovsky E., Clardy J.C., Faulker D.J. Org. Lett. 4:2002;1699-1702.
4. Fan X., Flentke G.R., Rich D.H. J. Am. Chem. Soc. 120:1998;6321.
5. Jia Y.X., Wu B., Li X., Ren S.K., Tu Y.Q., Chan A.S.C., Kitching W. Org. Lett. 3:2001;847-849.
6. Jia Y.X., Li X., Wu B., Zhao X.Z., Tu Y.Q. Tetrahedron. 58:2002;1697-1708.
7. Waddell T.G., Ross P.A. J. Org. Chem. 52:1987;4802-4804.
8. Misono M., Nojiri N. Appl. Catal. 64:1990;1-30.
9. 1H NMR NOE experiment.
10. Nicolaou K.C., Xu J.Y., Kim S., Pfefferkorn J., Ohshima T., Vourloumis D., Hosokawa S. J. Am. Chem. Soc. 120:1998;8661-8673.
11. Engman L., Stern D. J. Org. Chem. 59:1994;5179-5183.
12. Parker R.E., Isaacs N.S. Chem. Rev. 59:1959;737-799.
13. Kolb H.C., VanNieuwenhze M.S., Sharpless K.B. Chem. Rev. 94:1994;2483-2547.
14. 8-H ( δ: 4.05 ppm).
15. Bhalerao U.T., Rapoport H. J. Am. Chem. Soc. 93:1971;5311-5313.
16. Kalsi P.S., Chhabra B.R., Singh J., Vig R. Synlett. 1992;425-426.
17. 6 (M + H) 627.3532; found 627.3523.