Abstract
The efficient and flexible syntheses of 5,8-disubstituted indolizidine poisonous-frog alkaloids is described using a highly stereoselective Michael-type conjugate addition reaction as the key step. In this work, syntheses of the 5,8-disubstituted indolizidine poisonous-frog alkaloids (–)-231C, (–)-221I and the proposed structure for (–)-193E are reported.
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References
1.
Daly J.W.
,
Spande T.F.
, and
Garraffo H.M.
, J. Nat. Prod. , 2005 , 68 , 1556 .
2.
Daly J.W.
, J. Med. Chem. , 2003 , 46 , 445 .
3.
Daly J.W.
,
Kaneko T.
,
Wilham J.
,
Garraffo H.M.
,
Spande T.F.
,
Espinosa A.
, and
Donelly M.
, Proc. Natl Acad. Sci. USA , 2002 , 99 , 13996 .
4.
Clark V.C.
,
Raxworthy C.J.
,
Rakotomalala V.
,
Sierwald P.
, and
Fisher B.L.
, Proc. Natl Acad. Sci. USA , 2005 , 102 , 11617 .
5.
Tsneki H.
,
You Y.
,
Toyooka N.
,
Kagawa S.
,
Kobayashi S.
,
Sasaoka T.
,
Nemoto H.
,
Kimura I.
, and
Dani J.A.
, Mol. Pharmacol. , 2004 , 66 , 1061 .
6.
Toyooka N.
,
Zhou D.J.
,
Nemoto H.
,
Garraffo H.M.
,
Spande T.F.
, and
Daly J.W.
, Tetrahedron Lett. , 2006 , 47 , 577 .
7.
Toyooka N.
,
Zhou D.J.
,
Nemoto H.
,
Garraffo H.M.
,
Spande T.F.
, and
Daly J.W.
, Tetrahedron Lett. , 2006 , 47 , 581 .
8.
Hodgkinson T.J.
, and
Shipman M.
, Synthesis , 1998 , 1141 .
9.
Comins D.L.
, and
Dehghani A.
, Tetrahedron Lett. , 1992 , 33 , 6299 .
10.
Toyooka N.
, and
Nemoto H.
, Recent Res. Dev. Org. Chem. , 2002 , 6 , 611 .
11.
Basha A.
,
Lipton M.
, and
Weinreb S.M.
, Tetrahedron Lett. , 1977 , 18 , 4171 .
12.
Stork G.
, and
Zhao K.
, Tetrahedron Lett. , 1989 , 30 , 2173
13.
Takahashi S.
,
Kuroyama Y.
,
Sonogashira K.
, and
Hagihara N.
, Synthesis , 1980 , 627 .
14.
Wolff S.
,
Schlegel H.
,
Whangbo M.H.
, and
Bernardi F.
, Can. J. Chem. , 1974 , 52 , 3787 .
15.
Hoffmann R.W.
, Chem. Rev. , 1989 , 89 , 1841 .
16.
Deslongchamps P.
, Stereoelectronic effects in organic chemistry , Pergamon , New York , 1983 , pp. 203 –290 .
17.
Cieplak A.S.
, J. Am. Chem. Soc. , 1981 , 103 , 4540 .