The total synthesis of racemic teucvin and 12-epi-teucvin

Angewandte Chemie - International Edition

Volumn 42, Issue 16, 2003, Pages 1851-1853

  Liu, Hsing Jang ^a,b,c   Zhu, Jia Liang ^a,b   Chen, I Chia ^a,b   Jankowska, Renata ^c   Han, Yongxin ^c   Shia, Kak Shan ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

^b INSTITUTE OF CHEMISTRY   (Taiwan)

^c UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Diels Alder reaction; Natural products; Terpenoids; Teucvin; Total synthesis

Indexed keywords

CHEMICAL REACTIONS; SYNTHESIS (CHEMICAL);

RACEMIN TEUCVIN;

AROMATIC COMPOUNDS;

12 TEUCVIN; CLERODANE DERIVATIVE; DITERPENOID; TEUCVIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; DIELS ALDER REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037693737     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200250681     Document Type: Article

References (16)

1. a) J. R. Hanson, Nat. Prod. Rep. 1989, 6, 347;
2. b) F. Seaman, F. Bohlmann, C. Zdero, T. J. Mabry, Diterpenes of Flowering Plants, Compositae (Asteraceae), Springer, Heidelberg, 1990;
3. c) A. T. Merritt, S. V. Ley, Nat. Prod. Rep. 1992, 9, 243;
4. d) T. Tokoroyama, J. Synth. Org. Chem. Jpn. 1993, 51, 1164;
5. e) M. Bruno, M. L. Bondi, S. Rosselli, F. Piozzi, M. R. Y. Al-Hillo, J. Nat. Prod. 2000, 63, 1029.
6. For a recent review, see: T. Tokoroyama, Synthesis 2000, 5, 611.
7. a) E. Fujita, I. Uchida, T. Fujita, J. Chem. Soc. Chem. Commun. 1973, 793;
8. b) E. Fujita, I. Uchida, T. Fujita, J. Chem. Soc. Perkin Trans. 1 1974, 1547;
9. c) I. Uchida, T. Fujita, E. Fujita, Tetrahedron 1975, 31, 841;
10. d) T. Kawashima, T. Nakastu, Y. Fukazawa, S. Ito, Heterocycles 1976, 5, 227;
11. e) T. Nakastu, S. Ito, T. Kawashima, Heterocycles 1981, 15, 241.
12. M. Rojas-Garciduenas, X. A. Dorninguez, Turrialba 1976, 26, 10.
13. J. Fayos, F. G. Francisco, C. Pascual, A. Perales, F. Piozzi, M. Rico, B. Rodriguez, G. Savona, J. Org. Chem. 1984, 49, 1789.
14. H. J. Liu, N. H. Al-Said, Heterocycles 1997, 46, 203.
15. H. J. Liu, Y. Han, Tetrahedron Lett. 1993, 34, 423.
16. CCDC-194235 (12) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+ 44)1223-336-033; or deposit@ccdc.cam.ac. uk).