Formal total synthesis of (±)-herbertene-1,13-diol and (±)-α-herbertenol via Ireland ester Claisen rearrangement and RCM reaction sequence

Synlett

Volumn , Issue 7, 2005, Pages 1173-1175

  Srikrishna, A ^a   Lakshmi, B Vasantha ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

( ) herbertenol; ( ) herbertene 1,13 diol; Ireland ester Claisen rearrangement

Indexed keywords

ALPHA HERBERTENOL; CARBON; CYCLOPENTANE; HERBERTANE DERIVATIVE; HERBERTENE 1,13 DIOL; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

CHEMICAL REACTION; CLAISEN REARRANGEMENT; CONFERENCE PAPER; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; ESTERIFICATION; OXIDATION; OZONOLYSIS; REACTION ANALYSIS; REDUCTION; REPRODUCIBILITY; RING CLOSING METATHESIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TECHNIQUE;

EID: 18744369978     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-865223     Document Type: Conference Paper

References (24)

1. Irita, H.; Hashimoto, T.; Fukuyama, Y.; Asakawa, Y. Phytochemistry 2000, 55, 247.
2. (a) Matsuo, A.; Yuki, S.; Nakayama, M. J. Chem. Soc., Chem. Commun. 1981, 864.
3. (b) Matsuo, A.; Yuki, S.; Nakayama, M.; Hayashi, S. Chem. Lett. 1982, 463.
4. (c) Asakawa, Y.; Matsuda, R.; Schofield, W. B.; Gradstein, S. R. Phytochemistry 1982, 27, 2471.
5. (d) Matsuo, A.; Yuki, S.; Nakayama, M. Chem. Lett. 1983, 1041.
6. (e) Matsuo, A.; Nakayama, N.; Nakayama, M. Phytochemistry 1985, 24, 777.
7. (f) Matsuo, A.; Yuki, S.; Nakayama, M. J. Chem. Soc., Perkin Trans. 1 1986, 701.
8. (a) Fukuyama, Y.; Kiriyama, Y.; Kodama, M. Tetrahedron Lett. 1996, 37, 1261.
9. (b) Fukuyama, Y.; Asakawa, Y. J. Chem. Soc., Perkin Trans. 1 1991, 2737.
10. (a) Boxall, R. J.; Ferris, L.; Grainger, R. S. Synlett 2004, 2379.
11. (b) Ng, D.; Yang, Z.; Garcia-Garibay, M. A. Org. Lett. 2004, 6, 645.
12. (c) Srikrishna, A.; Satyanarayana, G. Tetrahedron Lett. 2003, 44, 1027.
13. (d) Srikrishna, A.; Rao, M. S. Eur. J. Org. Chem. 2004, 499.
14. (e) Srikrishna, A.; Babu, N. C.; Rao, M. S. Tetrahedron 2004, 60, 2125; and references cited therein.
15. (a) Ireland, R. E.; Mueller, R. H. J. Am. Chem. Soc. 1972, 94, 5897.
16. (b) Ireland, R. E.; Wipf, P.; Armstrong, J. D. J. Org. Chem. 1991, 56, 650.
17. (c) Gilbert, J. C.; Yin, J.; Fakhreddine, F. H.; Karpinski, M. L. Tetrahedron 2004, 60, 51.
18. (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
19. (b) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3013.
20. (c) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
21. Achari, B.; Bandyopadhyay, S.; Basu, K.; Pakrashi, S. C. Tetrahedron 1985, 41, 107.
22. (a) Schreiber, S, L.; Liew, W.-F. Tetrahedron Lett. 1983, 24, 2363.
23. (b) Criegee, R. Ber. Bunsen-Ges. Phys. Chem. 1944, 77, 722.
24. Generation of the lithium enolate of the ester 6 with LDA and wanning up the reaction (or refluxing), or quenching with t-butyldimethylsilyl chloride and heating the resultant TBDMS enol ether, however, failed to generate the Ireland ester Claisen rearrangement product.