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

共 50 条

[1] Scalable Total Synthesis of (-)-Berkelic Acid by Using a Protecting-Group-Free Strategy
Fananas, Francisco J.
Mendoza, Abraham
Arto, Tamara
Temelli, Baris
Rodriguez, Felix
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (20) : 4930 - 4933
[2] Protecting-Group-Free Total Synthesis of Goniothalesdiol A
Li, Junpeng
Zheng, Huaiji
Su, Yingpeng
Xie, Xingang
She, Xuegong
SYNLETT, 2010, (15) : 2283 - 2284
[3] Asymmetric, Protecting-Group-Free Total Synthesis of (-)-Englerin A
Zhou, Qianghui
Chen, Xiaofei
Ma, Dawei
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (20) : 3513 - 3516
[4] Protecting-Group-Free Total Synthesis of Anticancer (±)-Melotenine A
Thanetchaiyakup, Adisak
Rattanarat, Hassayaporn
Aree, Sudaporn
Duangthongyou, Tanwawan
Nanok, Tanin
Chuanopparat, Nutthawat
Ngernmeesri, Paiboon
SYNTHESIS-STUTTGART, 2022, 54 (07): : 1850 - 1856
[5] Asymmetric, Protecting-Group-Free Total Synthesis of (+)-Caribenol A
Han, Jing-Chun
Liu, Lian-Zhu
Li, Chuang-Chuang
Yang, Zhen
CHEMISTRY-AN ASIAN JOURNAL, 2013, 8 (09) : 1972 - 1975
[6] An Expedient Protecting-Group-Free Total Synthesis of (±)-Dievodiamine
Unsworth, William P.
Kitsiou, Christiana
Taylor, Richard J. K.
ORGANIC LETTERS, 2013, 15 (13) : 3302 - 3305
[7] Protecting-Group-Free Total Synthesis of (±)-Subincanadine F
Chen, Pinhong
Cao, Lidong
Li, Chaozhong
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (19): : 7533 - 7535
[8] Protecting-group-free synthesis
Hoffmann, Reinhard W.
SYNTHESIS-STUTTGART, 2006, (21): : 3531 - 3541
[9] Protecting-Group-Free Total Synthesis of (E)- and (Z)-Alstoscholarine
Gerfaud, Thibaud
Xie, Chunsong
Neuville, Luc
Zhu, Jieping
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (17) : 3954 - 3957
[10] Protecting-Group-Free Total Synthesis of Aplykurodinone-1
Tang, Yu
Liu, Ji-tian
Chen, Ping
Lv, Ming-can
Wang, Zhen-zhen
Huang, Yi-kun
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (23): : 11729 - 11734

← 1 2 3 4 5 →