The first total synthesis of (-)-tamandarin A |
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Authors: | Liang B Portonovo P Vera M D Xiao D Joullié M M |
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Institution: | Department of Chemistry, University of Pennsylvania, Philadelphia 19104-6323, USA. |
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Abstract: | formula: see text] Tamandarin A (1), a newly isolated natural product similar in structure to didemnin B (2), was shown to be somewhat more active in vitro than 2 against pancreatic carcinoma with an ED50 value 1.5 to 2 ng/mL. We report here the first total synthesis of 1. The key steps include a practical stereoselective synthesis of the Hiv-isostatine unit, high-yielding linear precursor formation, a successful macrocyclization, and coupling of the macrocycle with the side chain to afford tamandarin A (1). |
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