Synthetic study toward the total synthesis of marinomycins: Antitumor- antibiotics

ORGN 781

Anita Alni, alni@pmail.ntu.edu.sg and Teck-Peng Loh, teckpeng@ntu.edu.sg. Division of Chemistry and Biological Chemistry, Nanyang Technological University, Singapore City, 637371, Singapore
Marinomycins A-D were first isolated from saline culture of marine actinomycetes (Marinispora). Marinomycins A-D which are geometrical isomers, are new structure class of compounds that show significant antibiotic activities and selective cancer cell cytotoxicities. The unique structural features of this compound includes a macrolides composed of dimeric 2-hydroxy-6-alkenyl-benzoic acid lactones and conjugated tetraene-pentahydroxy polyketide chains which isomerizes to its geometrical isomers in room light. Our strategy to construct the molecule is using Wittig and Grubb's metathesis reaction followed by macrolactonization as the key step.