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Synfacts 2005(3): 0351-0351
DOI: 10.1055/s-2005-921615
DOI: 10.1055/s-2005-921615
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York
Total Synthesis of TANDEM on Solid Phase
J. P. Malkinson*, M. K. Anim, M. Zloh, M. Searcey*, A. J. Hampshire, K. R. Fox
University of London, and University of Southampton, UK
Further Information
Publication History
Publication Date:
22 November 2005 (online)
Significance
The total synthesis of N-demethylated triostin A (TANDEM), a C 2-symmetric bicyclic octadepsipeptide, on solid phase was successfully achieved in 22 steps (19 steps on solid phase) in an overall yield of 18%. Starting from N-Fmoc-alanine attached to Wang resin, seven amino acids and two chromophore moieties were successively incorporated in an alphabetical order [(a)-(i)]. The octadepsipeptide chain was then released from the resin by acidolysis using TFA (j), and macrolactamization of the resulting octadepsipeptide (k) followed by disulfide bond formation (l) gave TANDEM. DNase I footprinting analyses showed the ability of TANDEM to bind to DNA with a preference for 5′-TpA sequences.