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Diastereoselective Synthesis of trans-anti-Hydrophenanthrenes via Ti-mediated Radical Cyclization and Total Synthesis of Kamebanin
| Title: | Diastereoselective Synthesis of trans-anti-Hydrophenanthrenes via Ti-mediated Radical Cyclization and Total Synthesis of Kamebanin |
| Authors: | Suzuki, Takahiro Browse this author →KAKEN DB | | Ikeda, Wataru Browse this author | | Kanno, Ayaka Browse this author | | Ikeuchi, Kazutada Browse this author | | Tanino, Keiji Browse this author →KAKEN DB |
| Keywords: | diastereoselectivity | | ent-Kaurenes | | natural product | | radical cyclization | | total synthesis |
| Issue Date: | 22-Mar-2023 |
| Publisher: | Wiley-Blackwell |
| Journal Title: | Chemistry-A European journal |
| Volume: | 29 |
| Issue: | 17 |
| Publisher DOI: | 10.1002/chem.202203511 |
| Abstract: | Ent-kaurenes consist of an ABC-ring based on a trans-anti-hydrophenanthrene skeleton and a D ring with an exomethylene. Highly oxygen-functionalized ent-kauren-15-ones have promising antiinflammatory pharmacological activity. In this study, we developed a novel diastereoselective synthesis of trans-anti-hydrophenanthrenes via a Ti-mediated reductive radical cyclization. We also demonstrated the applicability of this method by developing the first total synthesis of (+/-)-kamebanin (longest linear sequence; 17 steps, overall yield; 6.5 %). Furthermore, this synthesis provided a formal semi-pinacol rearrangement for the construction of the quaternary carbon at C8 and a novel Thorpe-Ziegler-type reaction for the construction of the D-ring. |
| Rights: | This is the peer reviewed version of the following article: Chemistry-A European journal Vol.29(17), which has been published in final form at https://doi.org/10.1002/chem.202203511. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/91495 |
| 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: 鈴木 孝洋
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