Abstract
The development in the strategies for elucidating the structures of natural products from 1916 to 2016 are reviewed revealing the transition from chemical to spectroscopic methods and using examples drawn from the chemistry of terpenoids and steroids.
References
1.
Hanson J.R.
(2001 ) Nat. Prod. Rep. , 18 , 607 –617 .
2.
Pregl F.
(1917 ) Die quantitative organische microanalysis. J. Springer , Berlin .
3.
Ruzicka L.
and
Meyer J.
(1921 ) Helv. Chim. Acta , 4 , 505 –510 .
4.
Hanson J.R.
(2015 ) J. Chem. Res. , 39 , 127 –133 .
5.
Ruzicka L.
,
Meyer J.
and
Mingazzini M.
(1922 ) Helv. Chim. Acta , 5 , 345 –368 .
6.
Bradfield A.R.
,
Hegda B.
,
Rao B.S.
, (1936 ) J. Chem. Soc. , 667 –675 .
7.
Fieser L.F.
and
Fieser M.
(1959 ) Steroids. Reinhold , New York , pp. 26 –89 .
8.
Harries C.
(1905 ) Ber. Dtsch. Chem. Ges. , 38 , 3985 –3995 .
9.
Karrer P.
,
Helfenstein A.
,
Wehrli H.
and
Wettstein A.
(1930 ) Helv. Chim. Acta , 13 , 1084 –1092 .
10.
Kuhn R.
,
Winterstein A.
and
Lederer E.
(1931 ) Hoppe-Seyler's Zeit. Physiol. Chem. , 197 , 141 –160 .
11.
Kuhn R.
and
Lederer E.
(1931 ) Ber. Dtsch Chem. Ges , 64 , 1349 –1359 .
12.
Martin A.J.P.
and
Synge R.L.M.
(1941 ) Biochem. J. , 35 , 1358 –1368 .
13.
James A.T.
and
Martin A.J.P.
(1952 ) Biochem. J. , 50 , 679 –690 .
14.
Ruzicka L.
(1959 ) Proc. Chem. Soc. , 341 –360 .
15.
Fieser L.F.
and
Campbell W.P.
(1938 ) J. Am. Chem. Soc. , 60 , 159 –168 .
16.
Woodward R.B.
(1941 ) J. Am. Chem. Soc. , 63 , 1123 –1126 .
17.
Woodward R.B.
(1942 ) J. Am. Chem. Soc. , 64 , 72 –75 .
18.
Grove J.F.
and
Willis H.A.
(1951 ) J. Chem. Soc. , 877 –883 .
19.
Shoolery J.N.
and
Rogers M.T.
(1958 ) J. Am. Chem. Soc. , 80 , 5121 –5125 .
20.
Shoppee C.W.
(1947 ) Ann. Rep. Chem. Soc. , 43 , 200 –231 .
21.
Barton D.H.R.
and
Cookson R.C.
(1956 ) Quart. Rev. Chem. Soc. , 10 , 44 –82 .
22.
Barton D.H.R.
and
Jones E.R.H.
(1944 ) J. Chem. Soc. , 659 –665 .
23.
Birch A.J.
(1951 ) Ann. Rep. Chem. Soc. , 47 , 190 –205 .
24.
Bijvoet J.M.
,
Peerdeman A.F.
and
Van Bommel A.J.
(1951 ) Nature , 168 , 271 –272 .
25.
Djerassi C.
(1964 ) Proc. Chem. Soc. , 314 –330 .
26.
Budzikiewicz H.
,
Djerassi C.
and
Williams D.H.
(1964 ) Structure elucidation of natural products by mass spectrometry , Vols 1 and 2 . Holden-Day , San Fransico .
27.
MacMillan J.
,
Pryce R.J.
,
Eglinton G.
and
McCormick A.
(1967 ) Tetrahedron Lett. , 8 , 2241 –2243 .
28.
MacMillan J.
(2002 ) J. Plant. Growth Reg. , 20 , 387 –442 .
29.
Grove J.F.
(1961 ) Quart. Rev. Chem. Soc. , 15 , 56 –70 .
30.
Barton D.H.R.
and
de Mayo P.
(1957 ) Quart. Rev. Chem. Soc. , 11 , 189 –211 .
31.
Halsall T.G.
and
Theobald D.W.
(1962 ) Quart. Rev. Chem. Soc. , 16 , 101 –115 .
32.
Barton D.H.R.
,
Cheung H.T.
,
Cross A.D.
, (1961 ) J. Chem. Soc. , 5061 –5073 .
33.
Barton D.H.R.
,
Overton K.H.
and
Wylie A.
(1962 ) J. Chem. Soc. , 4809 –4815 .
34.
Barton D.H.R.
,
Pradhan S.K.
,
Sternhell S.
and
Templeton J.F.
(1961 ) J. Chem. Soc. , 255 –275 .
35.
Hanson J.R.
(2015 ) Sci. Prog. , 98 , 177 –188 .
36.
Ettre L.S.
(2000 ) Chromatographia , 51 , 7 –17 .
37.
Carter G.T.
(2014 ) Nat. Prod. Rep. , 31 , 711 –717 .
38.
Bouslimani A.
,
Sanchez L.M.
,
Garg N.
and
Dorrestein A.
(2014 ) Nat. Prod. Rep. , 31 , 718 –729 .
39.
Jarmusch A.K.
and
Cooks R.G.
(2014 ) Nat. Prod. Rep. , 31 , 730 –738 .
40.
Hites R.A.
(2016 ) Anal. Chem. , 88 , 6955 –6961 .
41.
Sadler I.H.
(1988 ) Nat. Prod. Rep. , 5 , 101 –127 .
42.
Derome A.E.
(1989 ) Nat. Prod. Rep. , 6 , 111 –141 .
43.
Breton R.C.
and
Reynolds W.F.
(2013 ) Nat. Prod. Rep. , 30 , 501 –524 .
44.
Dale J.A.
and
Mosher H.S.
(1973 ) J. Am. Chem. Soc. , 95 , 512 –519 .
45.
Guttormson R.
,
Main P.
,
Allison A.T.
and
Overton K.H.
(1970 ) Chem. Commun. , 719 .
46.
Zigon N.
,
Hoshino M.
,
Yoshioka S.
, (2015 ) Angew. Chem. (lnt. Ed.) , 54 , 9033 .
47.
Matsuda Y.
,
Mitsuhashi T.
,
Lee S.
, (2016 ) Angew. Chem. (lnt. Ed.) ., 55 , 5785 .
48.
Blunt J.W.
,
Copp B.R.
,
Keyzers R.A.
, (2015 ) Nat. Prod. Rep. , 32 , 116 –211 .
49.
Wang L.
,
Yang B.
,
Lin X.-P.
, (2013 ) Nat. Prod. Rep. , 30 , 455 –473 .
50.
Pickett J.
,
Allemann R.K.
and
Birkett M.A.
(2013 ) Nat. Prod. Rep. , 30 , 1277 –1283 .
51.
Fraga B.M.
(2013 ) Nat. Prod. Rep. , 30 , 1226 –1264 .
52.
Kong L.Y.
and
Tan R.X.
(2015 ) Nat. Prod. Rep. , 32 , 1617 –1621 .
53.
Li R.
,
Morris-Natschke S.
and
Lee K.-H.
(2016 ) Nat. Prod. Rep. , 33 , 1166 –1226 .
54.
Kingston D.G.L.
(2001 ) Chem. Commun. , 867 –880 .
55.
Bilton J.N.
,
Broughton H.B.
,
Jones P.S.
, (1987 ) Tetrahedron , 43 , 2805 –2815 .
56.
Ceunen S.
and
Geuns J.M.C.
(2013 ) J. Nat. Prod. , 76 , 1201 –1228 .
57.
Fattorusso C.
,
Stendardo E.
,
Appendino G.
, (2007 ) Org. Lett. , 9 , 2377 –2380 .
58.
Wang B.
,
Dossey A.T.
,
Walse S.S.
, (2009 ) J. Nat. Prod. , 72 , 709 –713 .
59.
Saielli G.
,
Nicolaou K.C.
,
Ortiz A.
, (2011 ) J. Am. Chem. Soc. , 133 , 6072 –6077 .
