Total synthesis of ailanthoidol and precursor XH14 by stille coupling

Journal of Organic Chemistry

Volumn 68, Issue 7, 2003, Pages 2968-2971

  Lin, Shun Yu ^a   Chen, Chih Lung ^a   Lee, Yean Jang ^a  

^a NATIONAL CHANGHUA UNIVERSITY OF EDUCATION   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

STILLE COUPLING;

ALDEHYDES; BROMINE COMPOUNDS; MEDICINE;

SYNTHESIS (CHEMICAL);

AILANTHOIDOL; BENZOFURAN DERIVATIVE; BROMIDE; HERBACEOUS AGENT; ORGANOTIN COMPOUND; PALLADIUM; SALVIA MILTIORRHIZA EXTRACT; UNCLASSIFIED DRUG; ZANTHOXYLUM AILANTHOIDOS EXTRACT;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; CHINESE MEDICINE; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TRANSFORMATION; HYDROGENATION; REDUCTION; STILLE REACTION;

BENZALDEHYDES; BENZOFURANS; CATALYSIS; DRUGS, CHINESE HERBAL; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; STEREOISOMERISM; ZANTHOXYLUM;

EID: 0037419454     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020653t     Document Type: Article

References (18)

1. Sheen, W. S.; Tsai, I. L.; Teng, C. M.; Chen, I. S. Phytocheminstry 1994, 36, 213.
2. Yang, Z.; Hon, M. H.; Chui, K. Y.; Xu, H. M.; Lee, C. M.; Cui, Y. X.; Wong, H. N. C.; Poon, C. D.; Fung, B. M. Tetrahedron Lett. 1991, 32, 2061.
3. (a) Kao, C. L.; Chern, J. W. Tetrahedron Lett. 2001, 42, 1111.
4. (b) Kao, C. L.; Chern, J. W. J. Org. Chem. 2002, 67, 6772 and references therein.
5. (c) Yang, Z.; Liu, H. B.; Lee, C. M.; Chang, H. M.; Wong, H. N. C. J. Org. Chem. 1992, 57, 7248.
6. (d) Scammells, P. J.; Baker, S. P.; Beauglehole, A. R. Bioorg. Med. Chem. 1998, 8, 1517.
7. Kelly, T. R.; Szabados, A.; Lee, Y. J. J. Org. Chem. 1997, 62, 428.
8. Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813.
9. (a) See ref 1c.
10. (b) Bates, R. W.; Rama-Devi, T. Synlett 1995, 1151.
11. (c) Hutchinson, S. A.; Luetjens, H.; Scammells, P. J. Bioorg. Med. Chem. Lett. 1997, 7, 3081.
12. (d) Fuganti, C.; Serra, S. Tetrahedron Lett. 1998, 39, 5609.
13. (e) Lutjens, H.; Scammells, P. J. Tetrahedron Lett. 1998, 39, 6581.
14. (f) See refs 3a and 3b.
15. Tseng, T. H.; Tsheng, Y. M.; Lee, Y. J.; Hsu, H. L. J. Chin. Chem. Soc. 2000, 47, 1165 and references therein.
16. Kelly, T. R.; Lee, Y. J.; Mears, R. J. J. Org. Chem. 1997, 62, 2774.
17. Riegel, B.; Wittcoff, H. J. Am. Chem. Soc. 1946, 68, 1913.
18. For general experimental procedures, see: Lee, J. M.; Tseng, T. H.; Lee, Y. J. Synthesis 2001, 15, 2247. Elemental analyses were performed on a Heracus CHN-OS Rapid spectrometer in the Taichung Instrumentation Center, National Science Council, Taiwan.