The First Synthesis of Cynandione A

Abstract

Cynandione A was prepared from acetylbenzoquinone by conjugate addition, acylation and demethylation.

Keywords

cynandione A - acetylbenzoquinone - conjugate addition - acylation - demethylation

References

• 1 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 
• 2 Chandrasekaran K. Mehrabian Z. Spinnewyn B. Drieu K. Fiskum G. Brain Res.  2001,  922:  282 
• 3 Li L. Nie J. Shen Z. Wu W. Chen Z. Hao X. Planta Med.  2001,  67:  142 
• 4 Lin Y.-L. Wu Y.-M. Kuo Y.-H. Phytochemistry  1997,  45:  1057 
• 5 Lee MK. Yeo H. Kim J. Markelonis GJ. Oh TH. Kim YC. J. Neurosci. Res.  2000,  59:  259 
• 6a Kraus GA. Wu Y. An. Quim.  1995,  91:  394 
• 6b Kraus GA. Wu Y. Tetrahedron Lett.  1991,  32:  3803 
• 7 Zimmerman HE. Posteris RJ. J. Org. Chem.  1980,  45:  4876 
• 9 Baker RW. Kyasnoor RV. Sargent MV. Skelton BW. White AH. Aust. J. Chem.  2000,  53:  487 
• 10 Lin C.-N. Huang P.-L. Lu C.-M. Yen M.-H. Wu R.-R. Phytochemistry  1997,  44:  1359 

8

We assign the structure of the monoacetate based on the mass spectral fragmentation of M - H₂O, 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.