Scalable Protecting-Group-Free Total Synthesis of Resibufogenin and Bufalin

被引：0

作者：

Yu, Shaopeng ^{[1
]}

Zhang, Qiuheng ^{[1
]}

Zhong, Xueqing ^{[1
]}

Wang, Chao ^{[1
,2
]}

Shi, Wenqing ^{[1
]}

Zhuang, Jiahua ^{[1
]}

Zhang, Rui ^{[1
]}

Jin, Fangjie ^{[1
]}

Zhang, Jiange ^{[1
]}

Zhao, Qunfei ^{[1
]}

Chen, Gu-Zhou ^{[1
]}

Ye, Wenbo ^{[1
]}

Lin, Guo-Qiang ^{[1
,2
]}

机构：

[1] Shanghai Univ Tradit Chinese Med, Innovat Res Inst Tradit Chinese Med, Res Ctr Chiral Drugs, Shanghai 201203, Peoples R China

[2] Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 45期

基金：

中国国家自然科学基金;

关键词：

CARDIOTONIC STEROIDS; CARDIOACTIVE STEROIDS; BUFADIENOLIDES; CONVERSION; CARDENOLIDE; OUABAGENIN; RECEPTOR; ROUTE; PLANT;

D O I：

10.1021/acs.orglett.4c03433

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chemoenzymatic synthesis access to resibufogenin and bufalin was developed in seven steps without protecting groups. Starting with androstenedione (AD), an alpha-OH was introduced directly at C14 by hydroxylase P-450lun, which was further used as the directing group for hydrogenation to fully control the C17 configuration in the beta-orientation after Suzuki cross-coupling. Dehydration of 14 alpha-OH followed by an epoxidation delivered resibufogenin. Simultaneously, bufalin was also obtained via a challenging anaerobic Mukaiyama hydration.

引用

页码：9704 / 9709

页数：6

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