Cycloaddition of annulated cyclohexa-2,4-dienones and novel reduction of halogen at bridgehead: an expedient route to tetracyclo[6.5.2.02,7.09,13]pentadec-2(7),11-dien-14-one and framework of conidiogenol and conidiogenone

Tetrahedron

Volumn 65, Issue 38, 2009, Pages 7969-7974

  Singh, Vishwakarma ^a   Singh, Raj Bahadur ^a   Mobin, Shaikh M ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

Diels Alder cycloaddition; Oxa di methane rearrangement; Photochemical reaction; Spiroepoxycyclohexa 2,4 dienone

Indexed keywords

1,4 CYCLOHEXADIENE; 2,4 DIENONE DERIVATIVE; CONIDIOGENOL; CONIDIOGENONE; CYCLOPENTADIENE DERIVATIVE; DITERPENOID; HALOGEN; METHANE; TETRACYCLO[6.5.2.0 2,7.0 9,13]PENTADEC 2(7) 11 DIEN 14 ONE DERIVATIVE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLOADDITION; DEHALOGENATION; DIELS ALDER REACTION; PHOTOCHEMISTRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

ALNUS;

EID: 68549097954     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.07.051     Document Type: Article

References (27)

1. Roncal T., Cordobes S., Ugalde U., He Y., and Sterner O. Tetrahedron Lett. 43 (2002) 6799
2. Du L., Zhu T., Cai S., Wang F., Xiao X., and Gu Q. Tetrahedron 65 (2009) 1033
3. Kozaka T., Miyakoshi N., and Mukai C. J. Org. Chem. 72 (2007) 10147
4. Yen C.-F., and Liao C.-C. Angew. Chem., Int. Ed. 41 (2002) 4090
5. Hirst G.C., Johnson Jr. T.O., and Overman L.E. J. Am. Chem. Soc. 115 (1993) 2992
6. Mehta G., and Reddy M.S. Tetrahedron Lett. 31 (1990) 2039
7. Singh V. Acc. Chem. Res. 32 (1999) 324
8. Singh V., Sahu P.K., Singh R.B., and Mobin S.M. J. Org. Chem. 72 (2007) 10155
9. Nilsson J.L.G., Selander H., Sievertsson H., Skanberg I., and Svensson K. Acta Chem. Scand. 25 (1971) 94
10. Adler E., Brasen S., and Miyake H. Acta Chem. Scand. 25 (1971) 2055
11. Becker H.-D., Bremholt T., and Adler E. Tetrahedron Lett. 13 (1972) 4205
12. Singh V., Porinchu M., Vedantham P., and Sahu P.K. Org. Synth. 81 (2005) 171
13. Touzeau F., Arrault A., Guillaumet G., Scalbert E., Pfeiffer B., Rettori M., Renard P., and Merour J. J. Med. Chem. 46 (2003) 1962
14. House H.O. Modern Synthetic Reactions (1972), Benzamin/Cummings, Menlo Park, California pp 145
15. Zimmerman H.E., and Armesto D. Chem. Rev. 96 (1996) 3065
16. Demuth M. In: Padwa A. (Ed). Organic Photochemistry Vol. 11 (1991), Marcel-Dekker, New York, NY 37-97 and references therein
17. Demuth M., and Hisken W. Angew. Chem., Int. Ed. Engl. 24 (1985) 973
18. Schuster D.I. In: De Mayo P. (Ed). Rearrangements in Ground and Excited States Vol. 3 (1980), Academic, New York, NY 232
19. Reekie T.A., Austin K.A.B., Banwell M.G., and Willis A.C. Aust. J. Chem. 61 (2008) 94
20. Banwell M.G., Edward A.J., Harfoot G.J., and Jolliffe K.A. J. Chem. Soc., Perkin Trans. 1 (2002) 2439
21. Maiti B.C., Singh R., and Lahiri S. J. Photochem. Photobiol. A: Chem. 91 (1995) 27
22. Armesto D., Ortiz M.J., Romano S., Agarrabeitia A.R., Gallega M.G., and Ramos A. In: Horspool W.M., and Lenci F. (Eds). CRC Hand Book of Organic Photochemistry and Photobiology (2004), CRC, Boca Raton Chapter 95
23. Singh V. In: Horspool W.M., and Lenci F. (Eds). CRC Hand Book Organic Photochemistry and Photobiology (2004), CRC, Boca Raton Chapters 78 and 79
24. Enholm E.J., and Jia Z.J. J. Org. Chem. 62 (1997) 174
25. Trost B.M. Angew. Chem., Int. Ed. Engl. 34 (1995) 259
26. Corey E.J., and Cheng X.-M. The Logic of Chemical Synthesis (1989), John Wiley & Sons, New York, NY
27. Chanon M., Barone R., Baralotto C., Julliard M., and Hendrickson J.B. Synthesis (1998) 1559