The first total synthesis of (-)-tamandarin A.
[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).
Liang
B
B
Department of Chemistry, University of Pennsylvania, Philadelphia 19104-6323, USA.
Portonovo
P
P
Vera
M D
MD
Xiao
D
D
Joullié
M M
MM
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D047630:Depsipeptides; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis / Q000737:chemistry
D000970:Antineoplastic Agents; D047630:Depsipeptides; D010456:Peptides, Cyclic; C409142:tamandarin A