Abstract
A novel and facile method for the synthesis of 4H-cyclopenta[c]pyrrolo[1,2-b] isoquinolin-2(3H)-one has been developed by employing the [2, 3] Stevens rearrangement of methyl N-allyl-N-benzylpyrrolidine 2-carboxylate to methyl 2-allyl-l-benzyl-pyrrolidine 2-carboxylate and acid-lactonisation as key transformations. The synthetic strategy from readily available materials provided a model skeletal analogue of cephalotaxine and should have general applicability in the synthesis of Cephalotaxus alkaloids.
References
1.
Jalil Miah M.A.
,
Hudlicky T.
, and
Reed J. W.
, The alkaloids;
Brossi A.
, Ed., Academic Press : New York , 1998 , 51 , 199 .
2.
Keller L.
,
Dumas F.
, and
D'Angelo J.
, Eur. J. Org. Chem. , 2003 , 2488 .
3.
Wang Y.K.
,
Li Y. L.
,
Pan X. F.
,
Li S. W.
, and
Huang W. K.
, Acta Chim Sinica. , 1985 , 43 , 161 .
4.
Kantarjian H.M.
,
Talpaz M.
,
Santini V.
,
Murgo A.
,
Cheson B.
, and
O'Brien S. M.
, Cancer , 2001 , 92 , 1591 .
5.
Wang D.Z.
,
Ma G. E.
, and
Xu R. S.
, Acta. Pharm. Sinica. , 1992 , 27 , 178 .
6.
Yasuda S.
,
Yamada T.
, and
Hanaoka M.
, Tetrahedron Lett. , 1986 , 27 , 2023 .
7.
Sha C.K.
,
Yong J. J.
,
Yeh C. P.
,
Chang S. C.
, and
Wang S. L.
, J. Org. Chem. , 1991 , 56 , 2694 .
8.
Zhang N.
, and
Nubbemeyer U.
, Synthesis , 2002 , 242 .
9.
Ikeda M.
,
Hirose K.-I.
,
El Bialy S. A. A.
,
Sato T.
,
Yakura T.
, and
Bayomi S. M. M.
, Chem. Pharm. Bull. , 1998 , 46 , 1084 .
10.
Maeda K.
,
Miller R. A.
,
Szumigala R. H.
,
Shafiee Ali
Jr.
,
Karady S.
, and
Armstrong J. D.
III
, Tetrahedron Lett. , 2005 , 46 , 1545 .
11.
Kim K.M.
, and
Ryu E. K.
, Tetrahedron Lett. , 1996 , 37 , 1441 .
12.
Macritchie J.A.
,
Peakman T. M.
,
Silcock A.
, and
Willis C. L.
, Tetrahedron Lett. , 1998 , 39 , 7415 .
13.
Vanecko J.A.
,
Wan H.
, and
West F. G.
, Tetrahedron , 2006 , 62 , 1043 .
14.
Amonkar C.P.
,
Tilve S. G.
, and
Parameswaran P. S.
, Synthesis , 2005 , 14 , 2341 .
15.
Li W.-D. Z.
, and
Wang X.-W.
, Org. Lett. , 2007 , 9 , 1211 .