The first total synthesis of (-)-tamandarin A.

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).

• Authors: B Liang, P Portonovo, M D Vera, D Xiao, M M Joullié
• Journal: Organic letters (Org Lett) Vol. 1 Issue 8 Pg. 1319-22 (Oct 21 1999) ISSN: 1523-7060 [Print] United States
• PMID: 10825982 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, Non-P.H.S., Research Support, U.S. Gov't, P.H.S.)

Chemical References

• Antineoplastic Agents
• Depsipeptides
• Peptides, Cyclic
• tamandarin A

Topics

• Antineoplastic Agents (chemical synthesis, chemistry)
• Crystallography, X-Ray
• Depsipeptides
• Magnetic Resonance Spectroscopy
• Molecular Structure
• Peptides, Cyclic (chemical synthesis, chemistry)