Abstract
The synthesis of mansonone E was completed in six steps and 34% overall yield from commercially available starting material 3-bromo-4-methyl acetophenone. The thermal ring expansion of a cyclobutenedione derivative followed by an intramolecular 1,3-alkoxy exchange provided a facile route to the 1,2-naphthoquinone tricyclic structure of mansonone E.
References
1.
Bettòlo G.B.M.
,
Casinovi C.G.
, and
Galwfi C.
, Tetrahedron Lett. , 1965 , 52 , 4857 .
2.
Overeem J.C.
, and
Elgersma D.M.
, Phytochemistry , 1970 , 9 , 1949 .
3.
Boonsri S.
,
Katalal C.
,
Ponglimanont C.
,
Chantrapromma S.
, and
Kanjana-opas A.
, J. Nat. Prod. , 2008 , 71 , 1173 .
4.
Lee K.H.
,
Cho C.H.
, and
Rhee K.H.
, J. Med. Plants Res. , 2012 , 6 , 4091 .
5.
Zhang Y.
,
Liu Y.B.
,
Li Y.
,
Ma S.G.
,
Li L.
,
Qu J.
,
Zhang D.
,
Chen X.G.
,
Jiang J.D.
, and
Yu S.S.
, J. Nat. Prod. , 2013 , 76 , 1058 .
6.
Tiew P.
,
Takayama H.
,
Kitajima M.
,
Aimi N.
,
Kokpol U.
, and
Chavasiri W.
, Tetrahedron Lett. , 2003 , 44 , 6759 .
7.
Chen C.M.
,
Chen Z.T.
, and
Hong Y.L.
, Phytochemistry , 1990 , 29 , 980 .
8.
Kim J.P.
,
Kim W.G.
,
Koshino H.
,
Jung J.
, and
Yoo I.D.
, Phytochemistry , 1996 , 43 , 425 .
9.
Best W.M.
, and
Wege D.
, Tetrahedron Lett. , 1981 , 22 , 4877 .
10.
Best W.M.
, and
Wege D.
, Aust. J. Chem. , 1986 , 39 , 647 .
11.
Suh Y.G.
,
Shin D.Y.
,
Min K.H.
,
Hyun S.S.
,
Jung J.K.
, and
Seo S.Y.
, Chem. Commun. , 2000 , 10 , 1203 .
12.
Nunes R.L.
,
Bieber L.W.
, and
Longo R.L.
, J. Nat. Prod. , 1999 , 62 , 16435 .
13.
Moore H.W.
, and
Perri S.T.
, J. Org. Chem. , 1988 , 53 , 996 .
14.
Perri S.T.
,
Foland S.D.
,
Decker O.H.W.
, and
Moore H.W.
, J. Org. Chem. , 1986 , 51 , 3067 .
15.
Liebeskind L.S.
,
Iyer S.
, and
Jewell C.F.
, J. Org. Chem. , 1986 , 51 , 3065 .
16.
Liebeskind L.S.
, Tetrahedron , 1989 , 45 , 3053 .
17.
Packard E.
,
Pascoe D.D.
,
Maddaluno J.
,
Gonçalves T.P.
, and
Harrowven D.C.
, Angew. Chem. Int. Ed. , 2013 , 52 , 13076 .
18.
Iyer S.
, and
Liebeskind L.S.
, J. Am. Chem. Soc , 1987 , 109 , 2759 .
19.
Reed M.W.
,
Pollart D.J.
,
Perri S.T.
,
Foland L.D.
, and
Moore H.W.
,; J. Org. Chem. , 1988 , 53 , 2477 .
