TY - JOUR
T1 - Radical-Based Route to Functionalized Tetralin
T2 - Formal Total Synthesis of (±)-Hamigeran B
AU - Okanishi, Yusuke
AU - Ishikawa, Tohru
AU - Jinnouchi, Takuya
AU - Hayashi, Satoshi
AU - Takanami, Toshikatsu
AU - Aoyama, Hiroshi
AU - Yoshimitsu, Takehiko
N1 - Funding Information:
The authors acknowledge Professor Ichiro Hayakawa (Nihon University) for 2D NMR analysis and Professor Hiroki Kakuta (Okayama University) for UV-vis measurements. They also thank Kana Suzuki and Yuki Saku for their contribution to the preliminary part of this study. This work was supported by the Electric Technology Research Foundation of Chugoku and JSPS KAKENHI (grant nos. JP18K06578 and 21K06476).
Funding Information:
The authors acknowledge Professor Ichiro Hayakawa (Nihon University) for 2D NMR analysis and Professor Hiroki Kakuta (Okayama University) for UV–vis measurements. They also thank Kana Suzuki and Yuki Saku for their contribution to the preliminary part of this study. This work was supported by the Electric Technology Research Foundation of Chugoku and JSPS KAKENHI (grant nos. JP18K06578 and 21K06476).
Publisher Copyright:
© 2023 American Chemical Society.
PY - 2022
Y1 - 2022
N2 - A formal synthetic route to hamigeran B, an antiviral marine natural product with a unique tricyclic molecular architecture, has been developed. The key chemical transformations in the present route include a novel zinc(II)porphyrin-catalyzed photoredox radical cascade cyclization to access a functionalized tetralin, a catalyst-free benzylic radical bromination with NBS by visible-light irradiation, and a samarium(II)-induced cyclization of brominated tetralone possibly via an orthoquinodimethane-like intermediate.
AB - A formal synthetic route to hamigeran B, an antiviral marine natural product with a unique tricyclic molecular architecture, has been developed. The key chemical transformations in the present route include a novel zinc(II)porphyrin-catalyzed photoredox radical cascade cyclization to access a functionalized tetralin, a catalyst-free benzylic radical bromination with NBS by visible-light irradiation, and a samarium(II)-induced cyclization of brominated tetralone possibly via an orthoquinodimethane-like intermediate.
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U2 - 10.1021/acs.joc.2c02552
DO - 10.1021/acs.joc.2c02552
M3 - Article
AN - SCOPUS:85146180243
SN - 0022-3263
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
ER -
