Tetrahydroanthracene derivatives

Treatment of l,2-di(l-acetoxypropynyl)benzene (238) with Sml2 generates 1,2-dipropadienylbenzene (239), which spontaneously cyclizes to give 2,3-naphthoquino-dimethane (240). Then facile Diels-Alder reaction of 240 with fumarate (241) gives the tetrahydroanthracene derivative 242 [52]. 

With nickel(II) 2-ethylhexanoate and triethylaluminum, tetralin (59) is obtained by hydrogenation of naphthalene (55). Polycyclic aromatics, such as anthracene (57 equation 8), 9-methylanthracene and 9-trifluoroacetylanthracene, are partially hydrogenated to 1,2,3,4-tetrahydroanthracene derivatives by use of [Rh(DPPE)(arene)]+ in methanol and by ruthenium hydride complexes having triphenylphosphine ligands... 

Takido, M., S. Takahashi, K. Masuda, and K. Yasukawa Torosachrysone, a New Tetrahydroanthracene Derivative from the Seeds of Cassia torosa. Lloydia 40, 191 (1977). 

Chromomycin, mithramycin, and olivomycin are tetrahydroanthracene derivatives bearing two glycosidic side-chains. The strong binding to double-stranded DNA of these drugs at low concentrations has many characteristic features of the binding to DNA of actinomycin-D. It requires the presence of divalent cations in stoichiometric amounts. 

Tietze et al. reported the conceptually new domino process involving a combination of Tsuji-Trost and Heck reaction (Scheme 28) [72]. This reaction represents a powerful and flexible tool for the synthesis of substituted tetrahydroanthracenes. This method allows efficient access to tetrahydroan-thracene derivatives 94 in up to 89% isolated yield in a one-pot process starting from the diketone 93. 

This group comprises a large variety of types from simple anthraquinone dimers, as chrysotalunin, to combinations of an anthraquinone with an amino acid or a prenylated naphthol (e.g. laccaic acid C and dermocanarin I), tetrahydroanthracenes and -anthraquinones such as setomimycin and julichrome Ql, as well as to compounds with multiple cross-links as, for example, fagopyrin. Biogenetically the tetrahydro derivatives can be rather regarded as substituted naphthols. This is rather obvious e.g. with karviskione. Finally the anthraquinone moiety may combine with other oxygen heterocycles an in the case of euxanmodin A (Schemes 17 and 18). 

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