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Synthetic study on dolastatin 16: concise and scalable synthesis of two unusual amino acid units
| Title: | Synthetic study on dolastatin 16: concise and scalable synthesis of two unusual amino acid units |
| Authors: | Umezawa, Taiki Browse this author →KAKEN DB | | Sato, Akinori Browse this author | | Ameda, Yasuto Browse this author | | Casalme, Loida O. Browse this author | | Matsuda, Fuyuhiko Browse this author →KAKEN DB |
| Keywords: | Dolastatin 16 | | Unusual amino acid | | Total synthesis | | Mannich reaction | | Organocatalyst |
| Issue Date: | 1-Jan-2015 |
| Publisher: | Elsevier |
| Journal Title: | Tetrahedron letters |
| Volume: | 56 |
| Issue: | 1 |
| Start Page: | 168 |
| End Page: | 171 |
| Publisher DOI: | 10.1016/j.tetlet.2014.11.054 |
| Abstract: | A convenient and scalable synthesis of two unusual amino acid units found in dolastatin 16, dolaphenvaline, and dolamethylleuine, is described. Dolastatin 16, which was first isolated from the sea hare Dolabella auricularia by Pettit, exhibits not only strong inhibition of growth for a variety of human cancer cell lines but also potent antifouling activity against the larvae of the barnacle Balanus amphitrite. The key element of the synthesis is an organocatalytic Mannich reaction to construct two contiguous stereocenters in the amino acid units with almost complete enantio- and diastereoselectivity. |
| Rights: | © 2014 Elsevier Ltd. All rights reserved. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/58057 |
| Appears in Collections: | 環境科学院・地球環境科学研究院 (Graduate School of Environmental Science / Faculty of Environmental Earth Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 梅澤 大樹
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