Stereoselective synthesis of a versatile intermediate for the total synthesis of mono- and bis-THF containing annonaceous acetogenins

Tetrahedron Letters

Volumn 40, Issue 2, 1999, Pages 193-196

  Jan, S T ^a   Li, K ^a   Vig, S ^a   Rudolph, A ^a   Uckun, F M ^a  

^a PARKER HUGHES INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOGENIN; ALDEHYDE; EPOXIDE; TETRAHYDROFURAN DERIVATIVE; TRIDECANAL; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG MECHANISM; DRUG SYNTHESIS; EPOXIDATION; HYDROXYLATION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0033534337     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02222-9     Document Type: Article

References (19)

1. Jolad S.D. Hoffmann J.J. Schram K.H. Cole J.R. J. Org. Chem. 47 1982 3151 3153
2. Reviews: Cave A. Figadere B. Laurens A. Cortes D. Acetogenins from Annonaceae Herz W. Progress in the Chemistry of Organic Natural Products: Acetogenins from Annonaceae 1997 Springer-Verlag New York 81 288
3. Zeng L. Ye Q. Oberlies N.H. Shi G. Gu Z.-M. He K. McLaughlin J.L. Nat. Prod. Rep. 1996 275 306
4. Gu Z.-M. Zhao G.X. Oberlies N.H. Zeng L. McLaughlin J.L. Romeo J.T. Annonaceous Acetogenins Amason J.T. Mata R. Recent Advances in Phytochemistry 1995 Plenum Press New York 249 310
5. Fang X.-P. Rieser M.J. Gu Z.-M. Zhao G.-X. McLaughlin J.L. Phytochem. Anal. 4 1993 27 48
6. Rupprecht Y.K. Hui J.-H. McLaughlin J.L. J. Nat. Prod. 53 1990 237
7. Synthetic reviews: Hoppe R. Scharf H.-D. Synthesis 1995 1447 1464
8. Koert U. Synthesis 1995 115 132
9. Figadere B. Acc. Chem. Res. 28 1995 359 365
10. Harmange J.-C. Figadere B. Tetrahedron: Asymmetry 4 1993 1711
11. Recent synthesis: Hanessian S. Grillo T.A. J. Org. Chem. 63 1998 1049 1057
12. Marshall J.A. Jiang H. Tetrahedron Lett. 39 1998 1493 1496
13. Marshall J.A. Hinkle K.W. Tetrahedron Lett. 39 1998 1303 1306 and references therein
14. Taber D.F. Bhamidipati R.S. Thomas M.L. J. Org. Chem. 59 1994 3442 3444
15. Oberlies N.H. Chang C.-J. McLaughlin J.L. J. Med. Chem. 40 1997 2102 2106
16. Wang Z.-M. Zhang X.-L. Sharpless K.B. Sinha S.C. Sinha-Bagchi A. Keinan E. Tetrahedron Lett. 33 1992 6407 6410
17. Trust R.I. Ireland R.E. Organic Synth. Coll. Vol. 6 1988 606
18. Rossiter B.E. Synthetic Aspects and Applications of Asymmetric Epoxidation Morrison J Asymmetric Synthesis 1985 Academic Press Orlando 193 246
19. Kolb H.C. VanNieuwenhze M.S. Sharpless K.B. Chem. Rev. 94 1994 2483 2547