Abstract
A new method for the reduction of iodosteroids to deoxysteroids has been developed using Zn, HCOOH and a catalytic amount of Aliquat 336 in water. In total, 13 iodosteroids were reduced in good to excellent yields. The higher solubilities of the substrates lead to the faster reactions, and the aqueous reaction was efficiently accelerated by granular polytetrafluoroethylene. The advantage of the aqueous system over eight organic solvents has also been demonstrated.
References
1.
Jyrkkärinne J.
,
Mäkinen J.
,
Gynther J.
,
Savolainen H.
,
Poso A.
, and
Honkakoski P.
, J. Med. Chem. , 2003 , 46 , 4687 .
2.
Numazawa M.
,
Mutsumi A.
,
Tachibana M.
, and
Hoshi K.
, J. Med. Chem. , 1994 , 37 , 2198 .
3.
Piazza P.
Eur. Pat. WO2012160 006 (A1), 2012 .
4.
Scheer I.
, and
Mosettig E.
, J. Am. Chem. Soc. , 1955 , 77 , 1820 .
5.
Arai H.
,
Watanabe B.
,
Nakagawa Y.
, and
Miyagama H.
, Steroids , 2008 , 73 , 1452 .
6.
Barton D.
,
Crich D.
,
Lobberding A.
, and
Zard S.Z.
, J. Chem. Soc., Chem. Commun. , 1985 , 646 .
7.
Odedra A.
,
Geyer K.
,
Gustafsson T.
,
Glimour R.
, and
Seeberger P.
, Chem. Commun. , 2008 , 3025 .
8.
Barton D.
,
Jang D.O.
, and
Jaszberenyi J.C.
, Tetrahedron , 1993 , 49 , 7193 .
9.
Spiegel D.A.
,
Wiberg K.B.
,
Schacherer L.N.
,
Medeiros M.R.
, and
Wood J.L.
, J. Am. Chem. Soc. , 2005 , 127 , 12513 .
10.
Barton D.
,
Jang D.O.
, and
Jaszberenyi J. Cs.
, J. Org. Chem. , 1993 , 58 , 6838 .
11.
Julia S.A.
, and
Lorne R.
, Tetrahedron , 1986 , 42 , 5011 .
12.
Yamazaki O.
,
Togo H.
,
Matsubayashi S.
, and
Yokoyama M.
, Tetrahedron , 1999 , 55 , 3735 .
13.
Medeiros M.R.
,
Schacherer L.N.
,
Spiegel D.A.
, and
Wood J.L.
, Org. Lett. , 2007 , 9 , 4427 .
14.
McDonald C.E.
,
Ramsey J.R.
,
Sampsell D.G.
,
Anderson L.A.
,
Krebs J.E.
, and
Smith S.N.
, Tetrahedron , 2013 , 69 , 2947 .
15.
Bose A.K.
, and
Mangiaracina P.
, Tetrahedron Lett. , 1987 , 28 , 2503 .
16.
Rothman E.S.
, and
Wall M.E.
, J. Am. Chem. Soc. , 1956 , 1744 .
17.
Yates P.
, and
Stiver S.
, Can. J. Chem. , 1987 , 65 , 2203 .
18.
Togo H.
,
Matsubayashi S.
,
Yamazaki O.
, and
Yokoyama M.
, J. Org. Chem. , 2000 , 65 , 2816 .
19.
Clive D.
, and
Yang W.
, J. Org. Chem. , 1995 , 60 , 2607 .
20.
Cui X.
,
Li B.
,
Liu T.
, and
Li C.
, Green Chem. , 2012 , 14 , 668 .
21.
He G.
,
Li B.
, and
Li C.
, J. Agric. Food Chem. , 2013 , 61 , 2913 .
22.
Lange G.L.
, and
Gottardo C.
, Synth. Commun. , 1990 , 20 , 1473 .
23.
Hayes R.K.
, and
Holden M.
, Aust. J. Chem. , 1982 , 35 , 517 .
24.
Castedo L.
,
Marcos C.F.
,
Monteagudo M.
, and
Tojo G.
, Synth. Commun. , 1992 , 22 , 677 .
25.
Fukuyama T.
,
Kawamoto T.
,
Kobayashi S.
,
Ryu I.
, and
Uehara S.
, Org. Lett. , 2010 , 12 , 1548 .
26.
Yi J.
,
Lu X.
,
Sun Y.
,
Xiao B.
, and
Liu L.
, Angew. Chem. Int. Ed. , 2013 , 52 , 12409 .
27.
Kirk D.N.
,
Toms H.C.
,
Douglas C.
,
White K.A.
,
Smith K.E.
,
Latif S.
, and
Hubbard R.W.P.
, J. Chem. Soc., Perkin Trans. 2 , 1990 , 9 , 1567 .
28.
Concepcion J.I.
,
Francisco C.G.
,
Freire R.
,
Hernandez R.
,
Salazar J.A.
, and
Suarez E.
, J. Org. Chem. , 1986 , 51 , 402 .
29.
Butler R.N.
,
Coyne A.G.
,
Cunningham W.J.
, and
Moloney E.M.
, J. Org. Chem. , 2013 , 78 , 3276 .
30.
Lipshutz B.H.
,
Isley N.A.
,
Fennewald J.C.
, and
Slack E.D.
, Angew. Chem. Int. Ed. , 2013 , 52 , 10952 .
31.
Pfenninger J.
,
Heuberger C.
, and
Graf W.
, Helv. Chim. Acta , 1980 , 63 , 2328 .
32.
Bauer P.E.
,
Nelson D.A.
,
Watt D.S.
,
Reibenspies J.H.
,
Anderson O.P.
,
Seifert W.K.
, and
Moldowan J.M.
, J. Org. Chem. , 1985 , 50 , 5460 .
33.
Kočovský P.
, and
Černý V.
, Collect. Czech. Chem. Commun. , 1981 , 46 , 446 .
34.
Daus M.A.
, and
Hirschmann H.
, J. Am. Chem. Soc. , 1953 , 75 , 3840 .
35.
Balakrishnan P.
, and
Bhattacharyya S.C.
, Indian J. Chem., Sect. B , 1976 , 14 , 73 .
36.
Gonzalez A.G.
,
Garcia Francisco C.
,
Freire Barreira R.
, and
Suarez Lopez E.
, An. Quim. , 1971 , 67 , 433 .
37.
Arnold W.
,
Meister W.
, and
Englert G.
, Helv. Chim. Acta , 1974 , 57 , 1559 .
38.
Bascoul J.
,
Cocton B.
,
Crastes P.A.
, Tetrahedron. Lett. , 1969 , 2401 .
39.
Jones D.N.
, and
Grayshan R.
, J. Chem. Soc., (C) , 1970 , 2421 .
40.
Fetizon M.
,
Golfier M.
, and
Gramain J.C.
, Bull. Soc. Chim. Fr. , 1968 , 275 .
41.
Crabb T.A.
,
Saul J.A.
, and
Williams R.O.
, J. Chem. Soc., Perkin Trans. 1 , 1981 , 1041 .
42.
Hanson J.R.
, and
Wadsworth H.J.
, J. Chem. Soc., Perkin Trans. 1 , 1980 , 933 .
43.
Bazin M.A.
,
Travert C.
,
Carreau S.
,
Raulta S.
, and
Kihel L.E.
, Bio. Med. Chem. , 2007 , 15 , 3152 .
44.
Arantes S.F.
,
Hanson J.R.
,
Liman M.D.
,
Manickavasagar R.
,
Uyanik C.
, J. Chem. Res., (M) , 1998 , 2381 .
45.
Arnold W.
,
Meister W.
, and
Englert G.
, Helv. Chim. Acta , 1974 , 57 , 1559 .
46.
Grimshaw J.
, and
Millar P.G.
, J. Chem. Soc. C , 1970 , 2324 .
47.
Arnold W.
,
Meister W.
, and
Englert G.
, Helv. Chim. Acta , 1974 , 57 , 1559 .
48.
Bodenberger A.
, and
Dannenberg H.
, Chem. Ber. , 1971 , 104 , 2389 .