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Synthesis and Biological Activity of Kalkitoxin and its Analogues
Total syntheses of kalkitoxin, isolated from the Caribbean <i>Lyngbya majuscula</i>, and its analogues, 3-<i>epi</i>-, 7-<i>epi</i>-, 8-<i>epi</i>-, 10-<i>epi</i>-, 10-<i>nor</i>-, and 16-<i>nor</i>-kalkitoxin,
were achieved via oxazolidinone-based diastereoselective 1,4-addition
reaction of a methyl group and efficient TiCl<sub>4</sub>-mediated
thiazoline ring formation as the key steps. The biological activities
of synthetic kalkitoxin and its analogues were evaluated with brine
shrimp