Abstract
Cynandione A was prepared from acetylbenzoquinone by conjugate addition, acylation
and demethylation.
Keywords
cynandione A - acetylbenzoquinone - conjugate addition - acylation - demethylation
References
<A NAME="RM07204SS-1">1 </A>
Kobayashi H.
Shin-Ya K.
Furihata K.
Nagai K.
Suzuki K.-I.
Hayakawa Y.
Seto H.
Yun B.-S.
Ryoo I.-J.
Kim J.-S.
Kim C.-J.
Yoo I.-D.
J. Antibiot.
2001,
54:
1019
<A NAME="RM07204SS-2">2 </A>
Chandrasekaran K.
Mehrabian Z.
Spinnewyn B.
Drieu K.
Fiskum G.
Brain Res.
2001,
922:
282
<A NAME="RM07204SS-3">3 </A>
Li L.
Nie J.
Shen Z.
Wu W.
Chen Z.
Hao X.
Planta Med.
2001,
67:
142
<A NAME="RM07204SS-4">4 </A>
Lin Y.-L.
Wu Y.-M.
Kuo Y.-H.
Phytochemistry
1997,
45:
1057
<A NAME="RM07204SS-5">5 </A>
Lee MK.
Yeo H.
Kim J.
Markelonis GJ.
Oh TH.
Kim YC.
J. Neurosci. Res.
2000,
59:
259
<A NAME="RM07204SS-6A">6a </A>
Kraus GA.
Wu Y.
An. Quim.
1995,
91:
394
<A NAME="RM07204SS-6B">6b </A>
Kraus GA.
Wu Y.
Tetrahedron Lett.
1991,
32:
3803
<A NAME="RM07204SS-7">7 </A>
Zimmerman HE.
Posteris RJ.
J. Org. Chem.
1980,
45:
4876
<A NAME="RM07204SS-8">8 </A>
We assign the structure of the monoacetate based on the mass spectral fragmentation
of M - H2 O, which we believe arises from the interaction between the acetyl group and the hydroxyl
on the neighboring ring (Figure
[2 ]
). This fragmentation is also observed in compounds 4 , 5 and 1 .
<A NAME="RM07204SS-9">9 </A>
Baker RW.
Kyasnoor RV.
Sargent MV.
Skelton BW.
White AH.
Aust. J. Chem.
2000,
53:
487
<A NAME="RM07204SS-10">10 </A>
Lin C.-N.
Huang P.-L.
Lu C.-M.
Yen M.-H.
Wu R.-R.
Phytochemistry
1997,
44:
1359