Psammaplin synthesis

Interestingly, treating bromotyrosine with TFAA in an autoclave at 80-120 °C, affords the corresponding 5(2//)-oxazolone that was used as an intermediate in the synthesis of psammaplin. ... 

Psammaplin A is a symmetrical bromotyrosine-derived disulfide dimer isolated from a marine sponge Psammalysilla, which exhibits in vitro antibacterial activity against methicillin-resistant Staphylococcus aureus (Figure 11.96). ° In order to find potent and structurally simplified analogs of psammaplin A that could be used as tools for SAR smdies, Nicolaou et al. undertook the combinatorial synthesis of a library of disulfide-containing molecules using a pool of 88 synthetic... 

Nicolaou, K.C., Hughes, R., Pfefferkom, JA., Barluenga, S., and Roeckec A.J. (2001) Combinatorial synthesis through disulfide exchange discovery of potent psammaplin A type antibacterial agents active against methidllin-resistant Staphylococcus aureus (MRSA). Chem. Eur. J., 7,4280-4295. 

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