Total synthesis of 10-norparvulenone and of O-methylasparvenone using a xanthate-mediated free radical addition - Cyclization sequence

Organic Letters

Volumn 5, Issue 20, 2003, Pages 3717-3719

  Cordero Vargas, Alejandro ^a   Quiclet Sire, Béatrice ^a   Zard, Samir Z ^a  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

10 NORPARVULENONE; 10-NORPARVULENONE; 3 METHOXYPHENOL; 3-HYDROXYANISOLE; ANISOLE DERIVATIVE; ANTIVIRUS AGENT; FREE RADICAL; NAPHTHOL DERIVATIVE; O METHYLASPARVENONE; O-METHYLASPARVENONE; SEROTONIN ANTAGONIST; TETRALIN DERIVATIVE; THIOKETONE; UNCLASSIFIED DRUG; XANTHIC ACID DERIVATIVE;

ADDITION REACTION; ARTICLE; CHEMISTRY; CYCLIZATION; DRUG CONFORMATION; DRUG SYNTHESIS; REACTION ANALYSIS; SYNTHESIS;

ANISOLES; CYCLIZATION; FREE RADICALS; NAPHTHOLS; TETRALONES; THIONES;

EID: 0142074819     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035394o     Document Type: Article

References (15)

1. Fukami, A.; Nakamura, T.; Kim, Y-P.; Shiomi, K.; Hyashi, M.; Nagai, T.; Yamada. H; Komiyama, K.; Omura, S. J. Antibiot. 2000, 53, 1215.
2. (a) Simpson, T. J.; Stenzel, D. J. J. Chem. Soc., Chem. Commun. 1981, 139. (b) Shan, R.; Stadler, M.; Anke, H.; Sterner, O. J. Nat. Prod. 1997, 60, 804.
3. (b) Shan, R.; Stadler, M.; Anke, H.; Sterner, O. J. Nat. Prod. 1997, 60, 804.
4. Bös, M.; Canesso, R.; Inoue-Ohga, N.; Nakano, A.; Takehana, Y.; Sleight, A. J. Bioorg. Med. Chem. 1997, 5, 2165.
5. Bös, M.; Stadler, H.; Wichmann, J.; Jenck, F.; Martin, J. R.; Moreau, J-L.; Sleight, A. J. Helv. Chim. Acta 1998, 81, 525.
6. Liard, A.; Quiclet-Sire, B.; Saicic, R. N.; Zard, S. Z. Tetrahedron Lett. 1997, 38, 1759.
7. (a) Zard, S. Z. Angew. Chem., Int. Ed. Engl. 1977, 36, 672.
8. (b) Zard, S. Z. In Radicals in Organic Synthesis; Renaud, P., Sibi, M., Eds.; Wiley VCH: Weinheim, 2001; p 90.
9. Swada, S.; Miyasaka, T.; Arakawa, K. Chem. Pharm. Bull. 1977, 25, 3370.
10. For a review, see: Jutz, A. Adv. Org. Chem. 1976, 9, 225.
11. Nagata, W.; Okada, K.; Aoki, T. Synthesis 1979, 365.
12. For reviews on the Prins reaction, see: (a) Adams, D. R.; Bhatnagar, S. P. Synthesis 1977, 661. (b) Arundale, E.; Mikeska, L. A. Chem. Rev. 1952, 51, 505.
13. For reviews on the Prins reaction, see: (a) Adams, D. R.; Bhatnagar, S. P. Synthesis 1977, 661. (b) Arundale, E.; Mikeska, L. A. Chem. Rev. 1952, 51, 505.
14. (a) Gross, H.; Rieche, A.; Mattey, G. Chem. Ber. 1963, 96, 308.
15. (b) Cresp, T. M.; Sargent, M. V.; Elix, J. A.; Murphy, D. P. H. J. Chem. Soc., Perkin Trans. 1 1973, 340.