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-00000083.xml
Synlett 2009(10): 1587-1590
DOI: 10.1055/s-0029-1217338
DOI: 10.1055/s-0029-1217338
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Ring Rearrangement Approach to the Synthesis of Benzo[b]quinolizine and Benzoindolizine Architectures
Further Information
Received
23 March 2009
Publication Date:
02 June 2009 (online)
Publication History
Publication Date:
02 June 2009 (online)
Abstract
An efficient ring rearrangement metathesis (RRM) approach to the synthesis of benzo[b]quinolizine and benzoindolizine systems from N-propargyl-phenanthridine derivatives is reported. A novel use of flash vacuum pyrolysis (FVP) for the Boc-deprotection of acid-sensitive substrates is also disclosed.
Key words
phenanthridine - alkene - ring-rearrangement metathesis - flash vacuum pyrolysis - skeletal diversity
- Supporting Information for this article is available online:
- Supporting Information
- 1
Connon SJ.Blechert S. Angew. Chem. Int. Ed. 2003, 42: 1900 - 2
Mori M. Adv. Synth. Catal. 2007, 349: 121 - 3
Kitamura T.Kuzuba Y.Sato Y.Wakamatsu H.Fujita R.Mori M. Tetrahedron 2004, 60: 7375 - 4
Donaldson LR.Haigh D.Hulme AN. Tetrahedron 2008, 64: 4468 - 5
Pettit GR.Venkatswamy G.Herald DL.Singh SB.Cragg GM.Schmidt JM.Boettner FE.Williams M.Sagawa Y. J. Nat. Prod. 1986, 49: 995 -
6a
Unver N. Phytochem. Rev. 2007, 6: 125 -
6b
Lewis JR. Nat. Prod. Rep. 1994, 11: 329 -
7a
Grynkiewicz G.Chohecka-Koryn E.Gadzikowska M.Chodkowska A.Jagiello-Wojtowicz E. Eur. J. Med. Chem. 2001, 951 -
7b
Panzer A.Joubert AM.Bianchi PC.Hamel E.Seegers JC. Eur. J. Cell. Biol. 2001, 80: 111 - 8
Donaldson LR. PhD Thesis The University of Edinburgh; UK: 2009. - 9
Compain P. Adv. Synth. Catal. 2007, 11: 1163 - 10
Bai C.Lu X.He R.Zhang W.Feng X. Org. Biomol. Chem. 2005, 3: 4139 - 11
Groaz E.Banti D.North M. Tetrahedron 2008, 64: 208 - 12
Nadany AE.Mckendrick JE. Synlett 2007, 1663 - 13
Winkler JD.Londregan AT.Hamann MT. Org. Lett. 2007, 9: 4467 - 14
Spandl RJ.Rudyk H.Spring DR. Chem. Commun. 2008, 26: 3001 - 15
Mori M.Wakamatsu H.Tonogaki K.Fujita R.Kitamura T.Sato Y. J. Org. Chem. 2005, 70: 1066 - 16
Wakamatsu H.Sato Y.Fujita R.Mori M. Adv. Synth. Catal. 2007, 349: 1231 - 17
Groaz E.Banti D.North M. Tetrahedron Lett. 2007, 48: 1927 - 18
Kaul R.Brouillette Y.Sajjadi Z.Hansford KA.Lubell WD. J. Org. Chem. 2004, 69: 6131 - 19
Miel H.Rault S. Tetrahedron Lett. 1997, 38: 7865 - 20
Hwu JR.Jain ML.Tsay SC.Hakimelahi GH. Tetrahedron Lett. 1996, 37: 2035 - 21
Routier S.Sauge L.Ayerbe N.Coudert G.Merour JY. Tetrahedron Lett. 2002, 43: 589 - 22
El Kazzouli S.Koubachi J.Berteina-Raboin S.Mouaddib A.Gillaumet G. Tetrahedron Lett. 2006, 47: 8575 -
23a
McNab H. Aldrichimica Acta 2004, 37: 19 -
23b
McNab H. Contemp. Org. Synth. 1996, 3: 373 -
24a
Sibi MP.Christensen J.Li B.Renhowe PA.
J. Org. Chem. 1992, 57: 4329 -
24b
Fishwick CWG.Storr RC.Manley PW. J. Chem. Soc., Chem. Commun. 1984, 19: 1304 - 25
Garber SB.Kingsbury JS.Gray BL.Hoveyda AH. J. Am. Chem. Soc. 2000, 122: 8168 - 26
Krause JO.Lubbad SH.Nuyken O.Buchmeiser MR. Macromol. Rapid Commun. 2003, 24: 875