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Asymmetric Total Synthesis of Brasilicardins
| Title: | Asymmetric Total Synthesis of Brasilicardins |
| Authors: | Yoshimura, Fumihiko Browse this author →KAKEN DB | | Itoh, Ryusei Browse this author | | Torizuka, Makoto Browse this author | | Mori, Genki Browse this author | | Tanino, Keiji Browse this author →KAKEN DB |
| Keywords: | brasilicardins | | Michael addition | | natural products | | quaternary stereocenters | | total synthesis |
| Issue Date: | 21-Dec-2018 |
| Publisher: | Wiley |
| Journal Title: | Angewandte Chemie International Edition |
| Volume: | 57 |
| Issue: | 52 |
| Start Page: | 17161 |
| End Page: | 17167 |
| Publisher DOI: | 10.1002/anie.201811403 |
| Abstract: | Brasilicardins, bacterial diterpenoid natural products that display highly potent immunosuppressive activity, are promising immunosuppressant drug candidates. Structurally, they can be described as hybrids of terpenoids, amino acids, and saccharides, and share a characteristic highly strained anti‐syn‐anti‐fused perhydrophenanthrene terpenoid scaffold (ABC‐ring system) with two quaternary asymmetric carbon atoms. A unified and stereoselective total synthesis of all four brasilicardins has been designed based on the strategic use of an intramolecular conjugate addition. The ABC‐ring system was initially constructed with high stereocontrol by novel intramolecular conjugate additions of Weinreb amides and in situ generated (Z)‐vinyl copper species. The late‐stage common intermediate was subjected to stereoselective installation of the amino acid component, followed by introduction of the saccharide unit via glycosylation to accomplish the total synthesis of brasilicardins A–D. Our synthesis offers opportunities to synthesize various brasilicardin analogues for biological and pharmacological investigations. |
| Rights: | This is the peer reviewed version of the following article:Angewandte Chemie (International ed.) 57(52) December 21 2018, pp.17161-17167 which has been published in final form at https://doi.org/10.1002/anie.201811403. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/76353 |
| Appears in Collections: | 理学院・理学研究院 (Graduate School of Science / Faculty of Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 吉村 文彦
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