The Claisen rearrangement followed by phenol oxidation: A simple route to naturally occurring benzoquinones including an ansa-bridged derivative related to the ansamycin antibiotics

Synlett

Volumn , Issue 11, 2002, Pages 1874-1876

  Davis, Christopher J ^a   Moody, Christopher J ^a  

^a UNIVERSITY OF EXETER   (United Kingdom)

Author keywords

Natural products; Oxidations; Phenols; Quinones; Rearrangements

Indexed keywords

ANSAMYCIN DERIVATIVE; ANTIBIOTIC AGENT; BENZOQUINONE DERIVATIVE; PHENOL;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGENATION; OXIDATION; REACTION ANALYSIS;

EID: 0036418007     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34877     Document Type: Article

References (23)

1. Thomson, R. H. Naturally Occurring Quinones, 4th Ed.; Blackie: London, 1997.
2. Martin, T.; Moody, C. J. J. Chem. Soc., Perkin Trans. 1 1988, 241.
3. Moody, C. J.; Swann, E. J. Chem. Soc., Perkin Trans. 1 1993, 2561.
4. For the use of a Claisen rearrangement in the synthesis of the natural benzoquinone 4-methoxydalbergione, see: Barnes, M. F.; Ollis, W. D.; Sutherland, I. O.; Gottlieb, O. R.; Magalhaes, M. T. Tetrahedron 1965, 21, 2707.
5. Isolation: Bloch, B.; Karrer, P. Vjschr. Naturforsch. Ges., Zürich 1927, 72, 1.
6. Isolation: Marini-Bettolo, G. B.; Monache, F. D.; daLima, O. G.; Coelho, S. D. Gazz. Chim. Ital. 1971, 101, 41.
7. For a recent synthesis see: Mabic, S.; Vaysse, L.; Benezra, C.; Lepoittevin, J. P. Synthesis 1999, 1127.
8. Isolation: Seki, K.; Kaneko, R. Chem. Ind. (London) 1975, 349.
9. Synthesis: Tao, Z.; Liu, J. Zhongguo Yiyao Gongye Zazhi 1991, 22, 57; Chem. Abstr., 1991, 115, 8400.
10. Capecchi, T.; de Koning, C. B.; Michael, J. P. J. Chem. Soc., Perkin Trans. 1 2000, 2681.
11. Bagnell, L.; Cablewski, T.; Strauss, C. R.; Trainor, R. W. J. Org. Chem. 1996, 61, 7355.
12. An, J. Y.; Bagnell, L.; Cablewski, T.; Strauss, C. R.; Trainor, R. W. J. Org. Chem. 1997, 62, 2505.
13. Kumar, H. M. S.; Anjaneyulu, S.; Reddy, B. V. S.; Yadav, J. S. Synlett 2000, 1129.
14. Daskiewicz, J. B.; Bayet, C.; Barron, D. Tetrahedron Lett. 2001, 42, 7241.
15. 4), filtered and evaporated. The crude product was purified by flash chromatography on silica, eluting with ethyl acetate and light petroleum (1:4)
16. 8 90.5-91°C.
17. For a total synthesis, see: Panek, J. S.; Xu, F.; Rondon, A. C. J. Am. Chem. Soc. 1998, 120, 4113.
18. For a total synthesis, see: Nakata, M.; Osumi, T.; Ueno, A.; Kimura, T.; Tamai, T.; Tatsuta, K. Bull. Chem. Soc. Jpn. 1992, 65, 2974.
19. For another RCM-based route to the ansamycins, see: Bach, T.; Lemarchand, A. Synlett 2002, 1302.
20. Kato, T.; Nagae, K.; Hoshikawa, M. Tetrahedron Lett. 1999, 40, 1941.
21. 1H NMR spectroscopic analysis does not allow the assignment of the major isomer.
22. The Claisen rearrangement of compounds similar to 9 has also been successfully carried out under microwave conditions (DMF, 150°C).
23. 2, Pd/C, EtOAc), followed by reoxidation of the hydroquinone, gives a single characterisable compound.