Journal
ORGANIC LETTERS
Volume 14, Issue 22, Pages 5720-5723Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol3027347
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Funding
- Carlsberg Foundation (Denmark)
- Australian Research Council [FF0668733]
- National Health and Medical Research Council [DP1096290]
- Australian Research Council [FF0668733, DP1096290] Funding Source: Australian Research Council
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The first total synthesis and three-dimensional solution structure are reported for sanguinamide A, a thiazole-containing cyclic peptide from the sea slug H. sanguineus. Solution phase fragment synthesis, solid phase fragment assembly, and solution macrocyclization were combined to give (1) in 10% yield. Spectral properties were identical for the natural product, requiring revision of its structure from (2) to (1). Intramolecular transannular hydrogen bonds help to bury polar atoms, which enables oral absorption from the gut.
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