Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis 2006(15): 2556-2562
DOI: 10.1055/s-2006-942468
DOI: 10.1055/s-2006-942468
PAPER
© Georg Thieme Verlag Stuttgart · New YorkRegiospecific Synthesis of Benzo[b]fluorenones via Ring Contraction by Benzil-Benzilic Acid Rearrangement of Benz[a]anthracene-5,6-diones
Further Information
Received
24 February 2006
Publication Date:
04 July 2006 (online)
Publication History
Publication Date:
04 July 2006 (online)
Abstract
A regiospecific route to benzo[b]fluorenones is described. The synthesis is based upon a one-pot, regiospecific benzannulation of 1,4-dipolar synthons with naphthoquinone monoketal and ring contraction of the generated benz[a]anthracene-5,6-diones through benzil-benzilic acid rearrangement.
Key words
1,4-dipolar synthons - benz[a]anthracene-5,6-diones - benzo[b]fluorenones - benzannulation - benzil-benzilic acid rearrangement
- 1a
Ito S.Matsuya T.Omura S.Otani M.Nakagawa A. J. Antibiot. 1970, 23: 315 - 1b
Cone MC.Seaton PJ.Halley KA.Gould SJ. J. Antibiot. 1989, 42: 179 - 1c
Seaton PJ.Gould SJ. J. Antibiot. 1989, 42: 189 - 1d
Gould SJ.Tamayo N.Melville CR.Cone MC. J. Am. Chem. Soc. 1994, 116: 2207 - 2
Cone MC.Melville CR.Gore MP.Gould SJ. J. Org. Chem. 1993, 58: 1058 - 3a
Shin-ya K.Furihata K.Teshima Y.Hayakawa Y.Seto H. Tetrahedron Lett. 1992, 33: 7025 - 3b
Gould SJ.Melville CR.Cone MC.Chen J.Carney JR. J. Org. Chem. 1997, 62: 320 - 4
Gould SJ.Melville CR. Bioorg. Med. Chem. Lett. 1995, 5: 51 - 5
Carney JR.Hong A.-T.Gould SJ. Tetrahedron Lett. 1997, 38: 3139 - 6
Aoyama T.Zhao W.Kojima F.Muraoka Y.Naganawa H.Takeuchi T.Aoyagi T. J. Antibiot. 1993, 46: 1471 - 7
M-Contelles J.Molina TM. Curr. Org. Chem. 2003, 7: 1433 - 8a
Mal D.Hazra NK. Tetrahedron Lett. 1996, 37: 2641 - 8b
Hauser FM.Zhou M. J. Org. Chem. 1996, 61: 5722 - 8c
Chuang CP.Wang SF. Synlett 1996, 829 - 8d
Kumamoto T.Tabe N.Yamaguchi K.Ishikawa T. Tetrahedron Lett. 2000, 41: 5693 - 8e
Mohri S.Stefinovic M.Snieckus V. J. Org. Chem. 1997, 62: 7072 - 8f
Koyama H.Kamikawa T. Tetrahedron Lett. 1997, 38: 3973 - 8g
Williams W.Sun X.Jebaratnam D. J. Org. Chem. 1997, 62: 4364 - 8h
Gore MP.Gould SJ.Weller DD. J. Org. Chem. 1992, 57: 2774 - 8i
Qabaja G.Jones GB. J. Org. Chem. 2000, 65: 7187 - 8j
Gonzalez-Cantalapiedra E.de Frutos O.Atienza C.Mateo C.Echavarren AM. Eur. J. Org. Chem. 2006, 1430 - 9
Morris JL.Becker CL.Fronczek FR.Daly WH.McLaughlin ML. J. Org. Chem. 1994, 59: 6484 - 10a
Mal D.Ghorai S.Hazra N. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2001, 40: 994 - 10b
Ghorai SK.Hazra NK.Mal D. Tetrahedron Lett. 1998, 39: 689 - 10c
Ghorai SK.Roy HN.Bandopadhyay M.Mal D. J. Chem. Res., Synop. 1999, 30 - 11
Mal D.Hazra KN.Murty KVSN.Majumdar G. Synlett 1995, 1239 - 12a
Gill GB. Comprehensive Organic Synthesis Vol. 3:Pattenden G. Pergamon; New York: 1991. 821. p.38 - 12b
Ott GD.Smith GG. J. Am. Chem. Soc. 1955, 77: 2325 - 13
Iwamoto H.Kobayashi Y.Kawatani T.Suzuki M.Fukazawa Y. Tetrahedron Lett. 2006, 47: 1519 - 14a
Mal D.Roy HN.Hazra NK.Adhikari S. Tetrahedron 1997, 53: 2177 - 14b
Hauser FM.Dorsch WA.Mal D. Org. Lett. 2002, 4: 2237 - 14c
Mal D.Patra A.Roy H. Tetrahedron Lett. 2004, 45: 7895 - 15
Majumdar GM.Pal R.Murty KVSN.Mal D. J. Chem. Soc., Perkin Trans. 1 1994, 309 - 16
Toda F.Tanaka K.Kagawa Y.Sakaino Y. Chem. Lett. 1990, 373 - 17
Atienza C.Mateo C.de Frutos O.Echavarren AM. Org. Lett. 2001, 3: 153 - 18
Mehta G.Venkateswaran RV. Tetrahedron 2000, 56: 1399 - 19
Kanth JVB.Periasamy M. J. Org. Chem. 1991, 56: 5964 - 20
Orita A.Hasegawa D.Nakano T.Otera J. Chem. Eur. J. 2002, 8: 2000 - 21
Collins CJ.Burr JG.Hess DN. J. Am. Chem. Soc. 1951, 73: 5176