Radical-Based Route to Functionalized Tetralin: Formal Total Synthesis of (±)-Hamigeran B

被引：1

作者：

Okanishi, Yusuke ^{[1
]}

Ishikawa, Tohru ^{[1
]}

Jinnouchi, Takuya ^{[1
]}

Hayashi, Satoshi ^{[2
]}

Takanami, Toshikatsu ^{[2
]}

Aoyama, Hiroshi ^{[3
]}

Yoshimitsu, Takehiko ^{[1
]}

机构：

[1] Okayama Univ, Grad Sch Med Dent & Pharmaceut Sci, Div Pharmaceut Sci, Okayama 7008530, Japan

[2] Meiji Pharmaceut Univ, Tokyo 2048588, Japan

[3] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 02期

关键词：

LIGHT PHOTOREDOX CATALYSIS; ORGANIC-MOLECULES; O-QUINODIMETHANES; (-)-HAMIGERAN B; PORPHYRINS; GENERATION;

D O I：

10.1021/acs.joc.2c02552

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：1085 / 1092

页数：8

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