Dictyopteris undulata

A number of bicyclofarnesyl hydroquinones have already been isolated from the brown seaweed Dictyopteris undulata. The parent acyclic compound (11) has now been found in the fresh alga. Two papers on the terminal functionalization of farnesyl derivatives have been published. These include the use of 2,4,4,6-tetrabromocyclohexadienone as an alternative to N-bromosuccinimide for the formation of the bromohydrin of the terminal double bond of methyl farnesoate... 

Originally presented as derivatives of drimane (Fenical et al., 1973), it was established and confirmed by stereoselective synthesis, that zonarol and its derivatives have the carbon skeleton of ent-drimane (Welch and Rao, 1977a, 1978). Zonarone and isozonarone - the quinonic equivalents of zonarol and isozonarol - were prepared by oxidation of the latter, but could be intermediates in the biosynthesis of cyclozonarone, chromazonarol, and iso-chromazonarol which were isolated from Dictyopteris undulata (Fenical and McConnell, 1975). The probable biogenetic relationships between these compounds are summarized in Figure 14.13 (Kurata, Taniguchi, and Suzuki, 1996). 

Cimino, G., De Stefano, S.. Fenical, W., Minale, L., and Sims, J.J. (1975) Zonaroic add from ihe brown seaweed Dictyopteris undulata (which is the same as zonarioides). Experientia, 31,1250-1251. 

Fenical, W. and McConnell, O. (1975) Chromazonarol and isochromazonarol, new chromanols from the brown seaweed Dictyopteris undulata. Experientia, 31,1004—1005. 

Kurata, K Taniguchi, K and Suzuki, M. (1996) Cydozonarone, a sesquiterpene-substituted benzoquinone derivative from the brown alga Dictyopteris undulata. Phytochemistry, 41, 749-752. 

Ochi, M., Kotsuki, H., Inoue, S., Taniguchi, M., and Tokoroyama, T. (1979a) Isolation of 2-(3,7,ll-trimethyl-2,6,10-dodecatrienyl)-hydroquinone from the brown seaweed Dictyopteris undulata. Chem. Lett., 831-832. 

Hashimoto, M., Aoki, K., Takahashi, M., Okrmo, T, Kurata, K., and Suzuki, M. (2002) Total synthesis of both enantiomers of dictyochromenol, an antifeedant from Dictyopteris undulata and their (Z)-isomers. Biosci. Biotechnol. Biochem., 66, 1915-1924. 

Several merosesquiterpenes having the carbon skeleton of ent-drimane were firstisolatedin1973 fi-omthe spedes Dictyopteris zonarioides and D. undulata. The aromatic part of these molecules is often a hydroquinone that can lead to tetracyclic compounds by intramolecular cydization. Zonaroic add and some other meroterpenes isolated from D. zonarioides come from a coupling withparo-hydroxybenzoic add. 

---