Abstract
A key goal of synthetic organic chemistry is the preparation of functional molecules
from simple starting materials as expeditiously as possible. Building on our efforts
to construct tripodal receptors featuring a cis -1,3,5-cyclohexane core, we have employed a tridirectional Minisci-type radical alkylation
reaction as a single-step method for the production of a series of new putative receptors.
Key words
radicals - receptors - bioorganic chemistry - heterocycles - host-guest systems
References
<A NAME="RC01107SS-1">1 </A>
Wender PA.
Miller BL. In Organic Synthesis: Theory and Applications
Vol. 2:
.
JAI Press;
Greenwich:
1993.
p.27-66
<A NAME="RC01107SS-2">2 </A>
Tajc SG.
Miller BL.
J. Am. Chem. Soc.
2006,
128:
2532
<A NAME="RC01107SS-3A">3a </A>
Fischbach MA.
Lin H.
Liu DR.
Walsh CT.
Nat. Chem. Biol.
2006,
2:
132
<A NAME="RC01107SS-3B">3b </A>
Rastetter WH.
Erickson TJ.
Venuti MC.
J. Org. Chem.
1980,
45:
5011
<A NAME="RC01107SS-3C">3c </A>
Corey EJ.
Bhattacharyya S.
Tetrahedron Lett.
1977,
1031
<A NAME="RC01107SS-3D">3d </A>
Pollock JR.
Neilands JB.
Biochem. Biophys. Res. Commun.
1970,
38:
989
<A NAME="RC01107SS-4A">4a </A>
Lavigne JJ.
Anslyn EV.
Angew. Chem. Int. Ed.
1999,
38:
3666
<A NAME="RC01107SS-4B">4b </A>
Chin J.
Walsdorff C.
Stranix B.
Oh J.
Chung HJ.
Park S.-M.
Kim K.
Angew. Chem. Int. Ed.
1999,
38:
2756
<A NAME="RC01107SS-5">5 </A>
Minisci F.
Bernardi R.
Bertini F.
Galli R.
Perchinummo M.
Tetrahedron
1971,
27:
3575
<A NAME="RC01107SS-6A">6a </A>
Fontana F.
Minisci F.
Barbosa MCN.
Vismara E.
J. Org. Chem.
1991,
56:
2866
<A NAME="RC01107SS-6B">6b </A>
Bennasar M.-L.
Roca T.
Griera R.
Bosch J.
Org. Lett.
2001,
3:
1697
<A NAME="RC01107SS-7A">7a </A>
Jain R.
Vaitilingam B.
Nayyar A.
Palde PB.
Bioorg. Med. Chem. Lett.
2003,
13:
1051
<A NAME="RC01107SS-7B">7b </A>
Vangapandu S.
Jain M.
Jain R.
Singh PP.
Bioorg. Med. Chem.
2004,
12:
2501
<A NAME="RC01107SS-7C">7c </A>
Vaitilingam B.
Nayyar A.
Palde PB.
Monga V.
Jain R.
Kaur S.
Singh PP.
Bioorg. Med. Chem.
2004,
12:
4179
<A NAME="RC01107SS-8">8 </A>
Kaur N.
Lu X.
Gershengorn MC.
Jain R.
J. Med. Chem.
2005,
48:
6162
<A NAME="RC01107SS-9">9 </A>
Hansen KB.
Springfield SA.
Desmond R.
Devine PN.
Grabowski EJJ.
Reider PJ.
Tetrahedron Lett.
2001,
42:
7353
<A NAME="RC01107SS-10">10 </A>
Barton DHR.
Crich D.
Motherwell WB.
J. Chem. Soc., Chem. Commun.
1983,
939
<A NAME="RC01107SS-11">11 </A>
Minisci F.
Vismara E.
Fontana F.
Morini G.
Serravalle M.
Giordano C.
J. Org. Chem.
1987,
52:
730
<A NAME="RC01107SS-12">12 </A>
Heinisch G.
Lötsch G.
Angew. Chem., Int. Ed. Engl.
1985,
24:
692
<A NAME="RC01107SS-13">13 </A>
Palde, P. B.; Gareiss, P. C.; Miller, B. L., manuscript in preparation.