Aeroplysinin synthesis

Scheme 9.10 Andersen and Faulkner s racemic synthesis of aeroplysinin-1 (84) [96],...

Adamantyl haUdes, reactions of 677 p-(l-Adamantyl)phenols, synthesis of 606, 607 Aerophobin-1, biosynthesis of 1315, 1316 Aeroplysinin-1, synthesis of 1327, 1328 Aerothionin, biosynthesis of 1315, 1316 Ageing, free-radical theory of 140, 141 Agent Orange 12... 

This oxidation has been used in a recent synthesis of ( )-aeroplysinin-I (7), a metaboUte of the marine sponges of the genus Verongia. Lead tetraacetate oxidation of (3) gave the acetoxy dienone (4). Direct reduction of (4) with... 

Hinterding, K., Knebel, A., Herrlich, P., and Waldmarm, H. (1998) Synthesis and biological evaluation of aeroplysinin analogues a new class of receptor tyrosine kinase inhibitors. Bioorg. Med. Chem., 6, 1153-1162. 

Quite surprisingly, the first attempt to demonstrate the conversion of tyrosine into bromotyrosine derivatives was unsuccessful (175). In that experiment, Verongia aerophoba failed to incorporate radioactivity from U- " C -L-tyrosine into aerothionin (68), aeroplysinin-1 (14) and the dienone 1. Inactive aerothionin (68) was also isolated when the sponge was fed with U- C -L-ornithine and CH3- C methionine. However, the sponge utihzed these amino acids for the synthesis of fatty acids. A very slow rate of biosynthesis might account for these results. 

---