Discodermia dissoluta

A collection of the deep-sea sponge Discodermia dissoluta from Grand Bahaman Island provided another example discodermide (88) [146]. The... 

Gunasekera, S. P, Gunasekera, M., and McCarthy, P. J., Discodermide a new bioactive macrocyclic lactam from the marine sponge Discodermia dissoluta, J. Org. Chem., 56, 4830, 1991. 

Locate all the tetrahedral stereogenic centers in discodermolide, a natural product isolated from the Caribbean marine sponge Discodermia dissoluta. Discodermolide is a potent tumor inhibitor, and shows promise as a drug for treating colon, ovarian, and breast cancers. 

Gunasekera SP, Gunasekera M, Longley RE, Schulte GK. Dis-codermolide a new bioactive polyhydroxylated lactone from the marine sponge Discodermia dissoluta. 1. Org. Chem. 1990 55 4912-4915. 

Lepourcelet, M., Chen, Y. N., France, D. S., et al. (2004). SmaU-molecule antagonists of the oncogenic Tcf/beta-catenin protein complex. Cancer Cell, 1,91-102. Gunasekera, A. P., Gunasekera, M., Longley, R. E., Schulte, G. K. (1990). Dis-codermolide a new bioactive polyhydroxylated lactone from the marine sponge Discodermia dissoluta. J. Org. Chem., 55, 4912-4915. 

Discodermolide (3) is a polypropionate-based unique compound isolated from the Caribbean deep-sea sponge Discodermia dissoluta. It is immunosuppressive as well as highly cytotoxic. More significantly, it stabilizes microtubules more potently than taxol. " Attempts at large-scale synthesis were carried out for clinical trials as an anticancer agent but the clinical trials were discontinued in 2005 due to its toxicity. ... 

Discodermolide is a unique polyketide isolated in 1990 by Gunasekera et al. at the Harbor Branch Oceanographic Institute from the Caribbean deep sea sponge Discodermia dissoluta [1-2]. Methanol/toluene (3 1) solvent extraction of the sponge yielded an extract that was partitioned between ethyl acetate and water. By silica gel and reverse-phase chromatography, (+)-discodermolide was purified from the ethyl acetate-soluble material and obtained as crystalline solid in 0.002% yield (w/w from frozen sponge). 

Discodermolide (36) is a cytotoxic polyketide isolated in low yield from the Caribbean sponge Discodermia dissoluta 44), The recent discovery that discodermolide shares the same microtubule-stabilising mechanism of antimitotic action as the clinically important anticancer drug, Taxol (paclitaxel), and retains activity against Taxol -resistant cancer cells has stimulated considerable interest (45,46). Due to the scarce supply of the natural material, the development of an efficient total synthesis (47-52) of (+)-discodermolide is needed to provide useful quantities for further testing, as well as enabling access to structurally simplified analogues. 

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