Total synthesis of (±)-β-chamigrene and (±)-laurencenone C via Ireland ester Claisen rearrangement and an intramolecular type II carbonyl ene reaction sequence

Tetrahedron

Volumn 64, Issue 46, 2008, Pages 10501-10506

  Srikrishna, A ^a   Babu, R Ramesh ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; BETA CHAMIGRENE; CARBON; CARBONYL DERIVATIVE; ESTER; LAURENCENONE C; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CLAISEN REARRANGEMENT; COLUMN CHROMATOGRAPHY; DEOXYGENATION; DRUG STRUCTURE; DRUG SYNTHESIS; ESTERIFICATION; HYDROLYSIS; ISOMERIZATION; OXIDATION; PRIORITY JOURNAL;

EID: 52949121389     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.08.095     Document Type: Article

References (23)

1. Dorta E., Diaz-Marrero A.R., Cueto M., D'Croz L., Mate J.L., and Darias J. Phytochemistry 45 (2004) 7065-7068
2. Ito S., Endo K., Yoshida T., Yatagai M., and Kodama M. J. Chem. Soc., Chem. Commun. (1967) 186-188
3. Ohta Y., and Hirose Y. Tetrahedron Lett. (1968) 2483-2485
4. Kennedy D.J., Selby I.A., and Thomson R.H. Phytochemistry 27 (1988) 1761-1766
5. For the isolation of laurencenone C from the German liverwort Marchantia polymorpha, see:. Asakawa Y., Tori M., Masuya T., and Frahm J.-P. Phytochemistry 29 (1990) 1577-1584
6. Martin J.D., Perez C., and Ravelo J.L. J. Am. Chem. Soc. 108 (1986) 7801-7811
7. Dias T., Brito I., Moujir L., Paiz N., Darias J., and Cueto M. J. Nat. Prod. 68 (2005) 1677-1679
8. Ireland R.E., Dow W.C., Godfrey J.D., and Thaisrivongs S. J. Org. Chem. 49 (1984) 1001-1013
9. Adams J., Lepine-Frenette C., and Spero D.M. J. Org. Chem. 56 (1991) 4494-4498
10. Hatsui T., Wang J.-J., and Takeshita H. Bull. Chem. Soc. Jpn. 67 (1994) 2507-2513
11. Srikrishna A., Lakshmi B.V., and Mathews M.M. Tetrahedron Lett. 47 (2006) 2103-2106
12. Chen Y.-J., Wang C.-Y., and Lin W.-Y. Tetrahedron 52 (1996) 13181-13188 and references cited therein
13. 13C spectral data for synthetic (±)-α-chamigrene reported by these authors is quite different from that reported by others. See,. Plamondon J., and Canonne P. Tetrahedron Lett. 32 (1991) 589-592
14. Clarke M.L., and France M.B. Tetrahedron 64 (2008) 9003-9031
15. Oppolzer W., and Snieckus V. Angew. Chem., Int. Ed. Engl. 17 (1978) 476-486
16. Taber D.F. Intramolecular Diels-Alder and Alder Ene Reactions (1984), Springer, Berlin
17. Ireland R.E., and Mueller R.H. J. Am. Chem. Soc. 94 (1972) 5897-5898
18. Ireland R.E., Wipf P., and Armstrong J.D. J. Org. Chem. 56 (1991) 650-657
19. Gilbert J.C., Yin J., Fakhreddine F.H., and Karpinski M.L. Tetrahedron 60 (2004) 51-60
20. Srikrishna A., and Ramesh Babu R. Tetrahedron Lett. 48 (2007) 6916-6919
21. 2 (1:1) under sonochemical irradiation gave 72 and 24% of 23 and 8, respectively, whereas 3 N HCl and THF (1:10) gave 32 and 36%, respectively. 20 mol % of TFA in 2:1 THF-water at rt gave 35 and 33% of 23 and 8, respectively.
22. Barton D.H.R., and Mc Combie S.W. J. Chem. Soc., Perkin Trans. 1 (1975) 1574-1585
23. Barton D.H.R., Crich D., Lobberding A., and Zard S.Z. Tetrahedron 42 (1986) 2329-2338