Stereoselective synthesis of (±)-(13E)-2-oxo-5α-cis-17α,20α-cleroda-3,13-dien-15-oic acid, an alleged cis-clerodane diterpenic acid

Tetrahedron Letters

Volumn 37, Issue 38, 1996, Pages 6869-6872

  Lee, Tsung Ho ^a   Liao, Chun Chen ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

anionic oxy Cope rearrangement; cis clerodane diterpenic acid; o benzoquinone, intramolecular Diels Alder reaction; Suzuki reaction

Indexed keywords

2 OXOCLERODA 3,13 DIEN 15 OIC ACID; CLERODANE DERIVATIVE; DITERPENE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY DIFFRACTION;

BETULACEAE; LATEOLABRAX JAPONICUS; OXY;

EID: 0030590409     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01500-6     Document Type: Article

References (21)

1. 1. Ley, S. V.; Merritt, A. T. Natural Product Reports 1992, 9, 243-287.
2. 2. (a) Tokoroyama, T. Yuki Gosei Kagaku Kyokai Shi 1993, 51, 1164-1177;
3. (b) Liu, H. J.; Shia, K. S.; Han, Y.; Wang, Y. Synlett 1995, 545-546;
4. (c) Piers, E.; Breau, M.; Han, Y.; Plourde, G. L.; Yeh, W. L. J. Chem. Soc., Perkin Trans, 1 1995, 963-964.
5. 3. Avila, D.; Medina, J. D. Phytochemistry 1991,30, 3474-3475.
6. 4. Lee, T. H.; Liao, C. C.; Liu, W. C. Tetrahedron Lett. 1996, in press.
7. 5. Liao, C. C.; Hwang, J. T. Tetrahedron Lett. 1991, 32, 6583-6586.
8. 6. Chu, C. S.; Lee, T. H.; Liao, C. C. Synlett 1994, 635-636.
9. 7. Hill, R. K. in Comprehensive Organic Synthesis; Paquette, L. A., Ed.; Pergamon: Oxford, 1991; Vol. 5.
10. 8. Metz, P.; Mues, C. Tetrahedron 1988, 44, 6841-6853.
11. 9. Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716.
12. 10. Negri, J. T.; Morwick, T.; Doyon, J.; Wilson, P. D.; Huckey, E. R.; Paquette, L. A. J. Am. Chem. Soc. 1993, 115, 12189-12190.
13. 11. Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357-1360.
14. 12. (a) Suzuki, A. Pure Appl. Chem. 1991, 63, 419-422;
15. (b) Suzuki, A.; Miyaura, N. Yuki Gosei Kagaku Kyokai Shi 1993, 51, 1043-1052.
16. 13. Johnson, C. R.; Braun, M. P. J. Am. Chem. Soc. 1993, 115, 11014-11015.
17. 14. Chalchat, J. C.; Theron, F.; Vessiere, R. C. R. Acad. Sci., Ser. C. 1971, 273, 763-765.
18. 15. Reuss, R. H.; Hassner, A. J. Org. Chem. 1975, 39, 1785-1787.
19. 2 × 3), 39.2 (C), 39.4 (C), 47.5 (CH), 115.5 (CH), 128.1 (CH), 162.4 (C), 169.4 (C), 171.5 (C), 199.1 (C).
20. 17. We thank Professor Shie-Ming Peng and Mr. Gene-Hsiang Lee for the X-ray diffraction study. The result will be published in a full paper in future.
21. 18. Welch, S. C.; Chou, C. Y.; Gruber, J. M.; Assercq, J. M. J. Org. Chem. 1985, 50, 2668-2676.