Synthesis of Mirabiquinone A: A Biquinone from the Sea Urchin Scaphechinus mirabilis and Related Compounds

Abstract

The first total synthesis of mirabiquinone A (2,3,5,6,8,10,11,13-octahydroxy-7-methyl-1H-dibenzo[b,h]xanthene-1,4,9,12(7H)-tetraone) produced by the sea urchin Scaphechinus mirabilis is described. This was achieved by cyclization of 6,6′-ethylidenebis(7-hydroxy-2,3-dimethoxynaphthazarin) or its mono- or dimethoxy derivatives and functional group deprotection. The synthesis of methyl analogues of mirabiquinone A is also described.

Key words

6,6′-ethylidenebis(2,3,7-trihydroxynaphthazarin) - cyclization - mirabiquinone A - dibenzo[b,h]xanthenetetraone - sea urchin Scaphechinus mirabilis

• References

• 1 Mischenko NP, Vasileva EA, Fedoreyev SA. Tetrahedron Lett. 2014; 55: 5967
• 2a Thomson RH. Naturally Occurring Quinones . 2nd ed. Academic Press; London: 1971
• 2b Thomson RH. Naturally Occurring Quinones . 3rd ed. Chapman & Hall; London: 1987
• 2c Thomson RH. Naturally Occurring Quinones . 4th ed. Blackie Academic and Professional; London: 1997
• 3 Mathieson JW, Thomson RH. J. Chem. Soc. C 1971; 153
• 4 Shikov AN, Ossipov VI, Martiskainen O, Pozharitskaya ON, Ivanova SA, Makarov VG. J. Chromatogr. A 2011; 1218: 9111
• 5 Pelageev DN, Panchenko MN, Pokhilo ND, Anufriev VPh. Russ. Chem. Bull. Int. Ed. 2010; 59: 1472
• 6 Kol’tsova EA, Denisenko VA, Maksimov OB. Chem. Nat. Compd. 1978; 14: 371
• 7 Anufriev VF, Chizhova AYa, Denisenko VA, Novikov VL. Zh. Org. Khim. 1993; 29: 2008 ; in Russian
• 8 Utkina NK, Shchedrin AP, Maksimov OB. Chem. Nat. Compd. 1976; 12: 387