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  • Title: Total synthesis of FR901464, an antitumor agent that regulates the transcription of oncogenes and tumor suppressor genes.
    Author: Albert BJ, Sivaramakrishnan A, Naka T, Koide K.
    Journal: J Am Chem Soc; 2006 Mar 08; 128(9):2792-3. PubMed ID: 16506745.
    Abstract:
    FR901464 is a potent anticancer agent that regulates the transcription of oncogenes and tumor suppressor genes. A convergent enantioselective synthesis of FR901464 was accomplished in 13 linear steps. Central to the synthetic approach was the diene-ene cross olefin metathesis reaction to generate the C6-C7 olefin, without the use of protecting groups, as the final coupling. Additional key reactions include a Zr/Ag-promoted alkynylation to set the C4 stereocenter, a mild and chemoselective Red-Al reduction, a stereoselective Mislow-Evans-type [2,3]-sigmatropic rearrangement to install the C5 stereocenter, a Carreira asymmetric alkynylation to generate the C4' stereocenter, and a highly efficient ring-closing metathesis-allylic oxidation sequence to form an unsaturated lactone.
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