Total synthesis of the threo, trans, threo-mono-tetrahydrofuran annonaceous acetogenin longifolicin

Tetrahedron Letters

Volumn 39, Issue 12, 1998, Pages 1493-1496

  Marshall, James A ^a   Jiang, Hongjian ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOGENIN; TETRAHYDROFURAN;

ARTICLE; SYNTHESIS;

EID: 0032546332     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00007-0     Document Type: Article

References (18)

1. 1. Review: Cavé, A.; Figadere, B.; Laurens, A.; Cortes, D. in Progress in the Chemistry of Natural Products, Herz, W.; Kirby, G.W.; Moore, R.E.; Steglich, W.; Tamm, Ch, Ed. Springer -Verlag, Vienna, 1997; pp 81-288.
2. 2. Ye, Q.; Alfonso, D.; Evert D.; McLaughlin, J.L. Bioorg. Med. Chem. 1996, 4, 537.
3. 3. Gu, Z-M.; Zeng, L.; Fang, X.-P.; Colman-Saizarbitoria, T.; Huo, M.; McLaughlin, J.L. J. Org. Chem. 1994, 59, 5162.
4. -7 μg/mL for lung, breast, and prostate human tumor cell lines
5. 1,4
6. 6. Reviews: Figadere, B. Accts. Chem. Res. 1995, 28, 359. Hoppe, R.; Scharf, H.-D. Synthesis 1995,1447. Marshall, J.A.; Hinkle K.W.; Hagedorn, C.E. Israel J. Chem. 1997, 37, 97. See also Hoye, R.R.; Ye, Z. J. Am. Chem. Soc. 1996, 37, 7001 and references cited therein.
7. 6. Reviews: Figadere, B. Accts. Chem. Res. 1995, 28, 359. Hoppe, R.; Scharf, H.-D. Synthesis 1995,1447. Marshall, J.A.; Hinkle K.W.; Hagedorn, C.E. Israel J. Chem. 1997, 37, 97. See also Hoye, R.R.; Ye, Z. J. Am. Chem. Soc. 1996, 37, 7001 and references cited therein.
8. 6. Reviews: Figadere, B. Accts. Chem. Res. 1995, 28, 359. Hoppe, R.; Scharf, H.-D. Synthesis 1995,1447. Marshall, J.A.; Hinkle K.W.; Hagedorn, C.E. Israel J. Chem. 1997, 37, 97. See also Hoye, R.R.; Ye, Z. J. Am. Chem. Soc. 1996, 37, 7001 and references cited therein.
9. 6. Reviews: Figadere, B. Accts. Chem. Res. 1995, 28, 359. Hoppe, R.; Scharf, H.-D. Synthesis 1995,1447. Marshall, J.A.; Hinkle K.W.; Hagedorn, C.E. Israel J. Chem. 1997, 37, 97. See also Hoye, R.R.; Ye, Z. J. Am. Chem. Soc. 1996, 37, 7001 and references cited therein.
10. 7. a) Marshall, J.A.; Hinkle, K.W. J. Org. Chem. 1997, 62, 5989.
11. b) Marshall, J.A.; Chen, M. J. Org. Chem. 1997, 62, 5996.
12. 9 (equation presented) ADD = 1,1′-(azodicarbonyl) dipiperidlne
13. 9. Cf. Marshall, J.A.; Welmaker, G.S.; Gung, B.W. J. Am. Chem. Soc. 1991, 113, 647.
14. 2AlH; 5) LiCl, MsCl, 2,6-lutidine as described in reference 7b.
15. 11. Vanhessche, K.P.M.; Wfing, Z.-M.; Sharpless, K.B. Tetrahedron Lett. 1994, 35, 3469.
16. 12. Yadav, J.S.; Chander, M.C.; Rao, C.S.; Tetrahedron Lett. 1989, 30, 5455.
17. 13. Garegg, P.J.; Samuelsson, B. J. Chem. Soc., Perkin I 1980, 2866.
18. 14. The alcohol of 97% ee is available from DMS Fine Chemicals Inc., Saddlebrook N.J.