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Synthesis 2004(8): 1262-1268
DOI: 10.1055/s-2004-822357
DOI: 10.1055/s-2004-822357
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Benzo[b]naphtho[2,3-d]furan-6,11-dione via One-pot Remote Anionic Fries Rearrangement and Metalation Reaction
Weitere Informationen
Received
26 March 2003
Publikationsdatum:
28. April 2004 (online)
Publikationsverlauf
Publikationsdatum:
28. April 2004 (online)
Abstract
The use of a lithiation reaction to transform the bromo-arylcarbamate 8a into the corresponding benzo[b]naphtho[2,3-d]furan-6,11-dione (2) is described.
Keywords
brazanquinones - metalation - tetracyclic - Fries rearrangement - synthesis
- 1
Liebermann C. Ber. Dtsch. Chem. Ges. 1899, 32: 916 - 2
Fruber O. Ber. Dtsch. Chem. Ges. 1937, 70: 1556 - 3
Sartori MF. J. Org. Chem. 1961, 26: 3152 - 4
Cheng CC.Dong Q.Liu L.Cheng A.Chiang Y.Savaraj N.Chou T. J. Med. Chem. 1993, 36: 4108 - 5
Fieser LF. Chemistry of Natural Products Related to Phenanthrene Reinbold Publishing Corp.; New York: 1937. p.20 - 6
Charttejea JN.Jha OP. J. Indian Chem. Soc. 1970, 47: 6 - 7
Charttejea JN. Experientia 1953, 9: 7 - 8
Jha OP. J. Indian Chem. Soc. 1973, 44: 740 - 9
Estévez RJ.Martinez E.Martinez L.Estévez JC.Castedo L. Tetrahedron Lett. 1998, 39: 2172 -
10a
Chauder BA.Lopes CC.Lopes RSC.Silva AJM.Snieckus V. Synthesis 1998, 279 -
10b
Nery MS.Ribeiro RP.Lopes CC.Lopes RSC. Synthesis 2003, 272 -
11a
Kalinin AV.Silva AJM.Lopes CC.Lopes RSC.Snieckus V. Tetrahedron Lett. 1998, 39: 4995 -
11b
Santos RP.Lopes CC.Lopes RSC. Synthesis 2001, 845 - 12
Mohri S.Stefinovic M.Snieckus V. J. Org. Chem. 1997, 62: 7072 - 13
Wang X.Benesch L.Bury P.Guillaneux D.Houldsworth S.Snieckus V. Tetrahedron Lett. 1998, 39: 961 - 14
Miki Y.Tada Y.Matsushita K. Heterocycles 1998, 48: 1593 - 15
Beak P.Snieckus V. Acc. Chem. Res. 1982, 15: 306 -
16a
De Silva SO.Watanabe M.Snieckus V. J. Org. Chem. 1979, 44: 4802 -
16b
Snieckus V. Chem. Rev. 1990, 90: 879 - 17
Beak P.Meyers A. Acc. Chem. Res. 1986, 6: 356 - 18
Klumpp GW.Kruithof KJH. Tetrahedron Lett. 1982, 23: 3101 - 19
King LC.Ostrum GK. J. Org. Chem. 1964, 29: 3459 - 20
Rap E. Ber. 1895, 29: 2810 -
21a
Lustig E.Benson WR.Duy N. J. Org. Chem. 1967, 32: 851 -
21b
Sibi MP.Chattopadhyay S.Dankwardt JW.Snieckus V. J. Am. Chem. Soc. 1985, 107: 6312 - 22
Zhang P.Gawley RE. J. Org. Chem. 1993, 58: 3223 -
23a
Elias VO.Simoneit BRT.Pereira AS.Cardoso JN. J. High Resol. Chromatogr. 1998, 21: 87 -
23b
Pereira AS.Pinto AC.Cardoso JN.Aquino Neto FR. J. High Resol. Chromatogr. 1998, 21: 396 - 24
Wakefield BJ. Organolithium Methods Academic Press Inc.; London: 1998. - 25
Gschwend HW.Rodriguez HR. In Organic Reactions Vol. 26: John Wiley & Sons; New York: 1979. p.1 - 26
Lutz RL.Rufus KA.Ashburn G.Bailey PS.Clark RT.Codington JF.Deinet AJ.Freek JA.Jordan RA.Leake NH.Martin TA.Nicodemus KC.Rowlett RJ.Shearer J.Smith D.Wilson JW. J. Org. Chem. 1947, 12: 664 - 27
Drake NL.Tuemmler WB. J. Am. Chem. Soc. 1954, 77: 1204