Title
Total Synthesis of Alloviroidin
Document Type
Article
Publication Date
4-5-2019
Abstract
Alloviroidin is a cyclic heptapeptide, produced by several species of Amanita mushrooms, that demonstrates high affinity for F-actin as is characteristic of virotoxins and phallotoxins. Alloviroidin was synthesized via a [3 + 4] fragment condensation of Fmoc-d-Thr(OTBS)-d-Ser(OTBS)-(2 S,3 R,4 R)-DHPro(OTBS)-OH and H-Ala-Trp(2-SOMe)-(2 S,4 S)-DHLeu(5-OTBS)-Val-OMe to form bond A. The linear heptapeptide favored a turn conformation, facilitating cyclization between Val and d-Thr (position B). Global deprotection and HPLC purification afforded alloviroidin with NMR spectra in excellent agreement with the natural product.
Publication Source (Journal or Book title)
Organic letters
First Page
2281
Last Page
2284
Recommended Citation
Taylor, C. M., Kutty, S. K., & Edagwa, B. J. (2019). Total Synthesis of Alloviroidin. Organic letters, 21 (7), 2281-2284. https://doi.org/10.1021/acs.orglett.9b00567