Abstract
This article reviews developments in the synthesis of isotopically-labelled samples of mevalonic acid for use in studies of terpenoid and steroid biosynthesis.
References
1.
Tavormina P.A.
,
Gibbs M.H.
, and
Huff J.W.
, J. Am. Chem. Soc. , 1956 , 78 , 4498 .
2.
Tavormina P.A.
, and
Gibbs M.H.
, J. Am. Chem. Soc. , 1956 , 78 , 6210 .
3.
Wolf D.E.
,
Hoffman C.H.
,
Aldrich P.E.
,
Skeggs H.R.
,
Wright L.D.
, and
Folkers K.
, J. Am. Chem. Soc. , 1956 , 78 , 4499 .
4.
Wolf D.E.
,
Hoffman C.H.
,
Aldrich P.E.
,
Skeggs H.R.
,
Wright L.D.
, and
Folkers K.
, J. Am. Chem. Soc. , 1957 , 79 , 1486 .
5.
Cornforth J.W.
,
Cornforth R.H.
,
Popjak G.
, and
Gore I.Y.
, Biochem. J. , 1957 , 66 , 10P .
6.
Cornforth J.W.
,
Cornforth R.H.
,
Popjak G.
, and
Gore I.Y.
, Biochem. J. , 1958 , 69 , 146 .
7.
Rilling H.C.
, and
Bloch K.
, J. Biol. Chem. , 1959 , 234 , 1424 .
8.
Wolstenholme G.E.W.
, and
O'Connor M.
(eds), CIBA Foundation Symposium on the Biosynthesis of Terpenes and Sterols , J.A. Churchill Ltd , London , 1959 .
9.
Goodwin T.W.
(ed.), Natural substances formed biologically from mevalonic acid Biochemical Society Symposium 29 , Academic Press , London , 1970 .
10.
Tamura G.
, and
Folkers K.
, J. Org. Chem. , 1958 , 23 , 772 .
11.
Rohmer M.
, Nat. Prod. Rep. , 1999 , 16 , 565 .
12.
Eberle M.
, and
Arigoni D.
, Helv. Chim. Acta , 1960 , 43 , 1508 .
13.
Cornforth R.H.
,
Cornforth J.W.
, and
Popjak G.
, Tetrahedron , 1962 , 18 , 1351 .
14.
Hoffman C.H.
,
Wagner A.F.
,
Wilson A.N.
,
Walton E.
,
Shunk C.H.
,
Wolf D.E.
,
Holly F.W.
, and
Folkers K.
, J. Am. Chem. Soc. , 1957 , 79 , 2316 .
15.
Shunk C.H.
,
Linn B.O.
,
Huff J.W.
,
Gilfillan J.L.
,
Skeggs H.R.
, and
Folkers K.
, J. Am. Chem. Soc. , 1957 , 79 , 3294 .
16.
Cornforth J.W.
,
Cornforth R.H.
,
Pelter A.
,
Horning M.G.
, and
Popjak G.
, Tetrahedron , 1959 , 5 , 311 .
17.
Gray W.F.
,
Deeth G.L.
, and
Cohen T.
, J. Org. Chem. , 1968 , 33 , 4532 .
18.
Ellison R.A.
, and
Bhaknager P.K.
, Synthesis , 1974 , 719 .
19.
Tanabe M.A.
, and
Peters R.H.
, Org. Synth. , 1981 , 60 , 92 .
20.
Sen S.
,
Tomita Y.
, and
Tori K.
, J. Chem. Soc., Chem. Commun. , 1975 , 270 .
21.
Evans R.
,
Hanson J.R.
, and
Nyfeler R.
, J. Chem. Soc., Perkin Trans. 1 , 1976 , 1214 .
22.
Cane D.E.
, and
Levin R.H.
, J. Am. Chem. Soc. , 1976 , 98 , 1183 .
23.
Lawson J.A.
,
Colwell W.T.
,
DeGraw J.J.
,
Peters R.H.
,
Dehn R.L.
, and
Tanabe M.
, Synthesis , 1975 , 729 .
24.
Hulcher F.H.
, and
Hosick T.A.
, US Patent 3,119,842, Chem. Abs. , 1964 , 60 , 10544 .
25.
Zamir L.O.
, and
Nguyen C.D.
, J. Labelled Compd. Radiopharm. 1987 , 24 , 1461 .
26.
Rousseau B.
,
Beaucourt J-P.
, and
Pichat L.
, J. Labelled Compd. Radiopharm. , 1983 , 20 , 537 .
27.
Scott A.I.
, and
Shishido K.
, J. Chem. Soc., Chem. Commun. , 1983 , 400 .
28.
Lewer P.
, and
MacMillan J.
, J. Chem. Soc., Perkin Trans. 1 , 1983 , 1417 .
29.
Escher S.
,
Loew P.
, and
Arigoni D.
, J. Chem. Soc., Chem. Commun. , 1970 , 823 .
30.
Fetizon M.
,
Golfier M.
, and
Louis J.-M.
, Tetrahedron , 1975 , 31 , 171 .
31.
Huang F.C.
,
Lee L.F.H.
,
Mittal R.S.D.
,
Ravikumar P.R.
,
Chan J.A.
,
Sih C.J.
,
Caspi E.
, and
Eck C.R.
, J. Am. Chem. Soc. , 1975 , 97 , 4144 .
32.
Francis C.J.
, and
Jones J.B.
, J. Chem. Soc., Chem. Commun. , 1984 , 579 .
33.
Lindberg M.
,
Yuan C.
,
DeWaard A.
, and
Bloch K.
, Biochemistry , 1962 , 1 , 182 .
34.
Cornforth J.W.
, and
Gray R.T.
, Tetrahedron , 1975 , 31 , 1509 .
35.
Popjak G.
,
Goodman D.S.
,
Cornforth J.W.
,
Cornforth R.H.
, and
Rhyage R.
, J. Biol. Chem. , 1961 , 236 , 1934 .
36.
Floss H.G.
,
Lin M.T.
,
Chang C-J.
,
Naidoo B.
,
Blair G.E.
,
Abou-Chaar C.I.
, and
Cassady J.M.
, J. Am. Chem. Soc. , 1974 , 96 , 898 .
37.
Ferraboschi P.
,
Canevotti R.
,
Grisenti P.
, and
Santaniello E.
, J. Chem. Soc., Perkin Trans. 1 , 1987 , 2301 .
38.
Yamauchi N.
,
Natsubari Y.
, and
Murae T.
, Bull. Chem. Soc. Jpn , 2000 , 73 , 2513 .
39.
Eguchi T.
,
Morita M.
, and
Kakinuma K.
, J. Am. Chem. Soc. , 1998 , 120 , 5427 .
40.
Eguchi T.
,
Watanabe E.
, and
Kakinuma K.
, Tetrahedron , 2003 , 59 , 6035 .
41.
Kishida M.
,
Yamauchi N.
,
Sawada K.
,
Ohashi Y.
,
Eguchi T.
, and
Kakinuma K.
, J. Chem. Soc. Perkin Trans. 1 , 1997 , 891 .
42.
Ackland M.J.
,
Hanson J.R.
, and
Ratcliffe A.H.
, J. Chem. Soc, Perkin Trans. 1 , 1984 , 2751 .
43.
Cornforth J.W.
,
Cornforth R.H.
,
Donninger C.
, and
Popjak G.
, Proc R. Soc., Ser. B , 1966 , 163 , 492 .
44.
Cornforth J.W.
,
Cornforth R.H.
,
Popjak G.
, and
Yengoyan L.
, J. Biol. Chem. , 1966 , 241 , 236 .
45.
Cornforth J.W.
,
Cornforth R.H.
,
Popjak G.
, and
Yengoyan L.
, J. Biol. Chem. , 1966 , 241 , 3970 .
46.
Schneider J.A.
, and
Yoshihara K.
, J. Org. Chem. , 1986 , 51 , 1077 .
47.
Ohta T.
,
Tabei N.
, and
Nozoe S.
, Heterocycles , 1989 , 28 , 425 .
48.
Popjak G.
, and
Cornforth J.W.
, Biochem. J. , 1966 , 101 , 553 .
49.
Scott A.I.
,
Phillips G.T.
,
Reichardt P.B.
, and
Sweeny J.G.
, J. Chem. Soc., Chem. Commun. , 1970 , 1396 .
50.
Blattmann P.
, and
Retey J.
, J. Chem. Soc., Chem. Commun. , 1970 , 1394 .
51.
Cornforth J.W.
,
Ross F.P.
, and
Wakselman C.
, J. Chem. Soc., Chem. Commun. , 1970 , 1395 .
52.
Cornforth J.W.
,
Ross F.P.
, and
Wakselman C.
, J. Chem. Soc., Perkin Trans, 1 , 1974 , 429 .
53.
Bonadies F.
,
Rossi G.
, and
Bonini C.
, Tetrahedron Lett , 1984 , 25 , 543 .
54.
Mori K.
, and
Okada K.
, Tetrahedron , 1985 , 41 , 557 .
55.
Ray W.C.
,
Raveendranath R.C.
, and
Spencer T.A.
, Tetrahedron , 1992 , 48 , 9427 .
56.
Mash E.A.
, and
Arterburn J.B.
, J. Org. Chem. , 1991 , 56 , 885 .
57.
Eliel E.L.
, and
Lynch J.E.
, Tetrahedron Lett. , 1981 , 28 , 2855 .
58.
Eliel E.L.
, and
Soal K.
, Tetrahedron Lett , 1981 , 28 , 2859 .
59.
Frye S.V.
, and
Eliel E.L.
, J. Org. Chem. , 1985 , 50 , 3402 .
60.
Sugai T.
,
Kakeya H.
, and
Ohta H.
, Tetrahedron , 1990 , 46 , 3463 .
61.
Ferraboschi P.
,
Grisenti P.
,
Casati S.
, and
Santaniello E.
, Synlett. , 1994 , 754 .
62.
Orru R.V.A.
,
Osprian I.
,
Kroutil W.
, and
Faber K.
, Synthesis , 1998 , 1259 .
63.
Shimizu M.
,
Kamikubo T.
, and
Ogasawara K.
, Tetrahedron: Asymmetry 1997 , 8 , 2519 .
64.
Lakner F.J.
, and
Hager L.P.
, J. Org. Chem. , 1996 , 61 , 3924 .
