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The First Total Synthesis of (−)-Tamandarin A

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journal contribution
posted on 16.09.1999, 00:00 by Bo Liang, Padma Portonovo, Matthew D. Vera, Dong Xiao, Madeleine M. Joullié
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).