Bioinspired Synthesis of Nortriterpenoid Propindilactone G

被引：40

作者：

Wang, Yu ^{[1
]}

Chen, Bo ^{[1
]}

He, Xubiao ^{[1
]}

Gui, Jinghan ^{[1
]}

机构：

[1] Univ Chinese Acad Sci, Chinese Acad Sci, Ctr Excellence Mol Synth, Shanghai Inst Organ Chem,CAS Key Lab Synthet Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2020年 / 142卷 / 11期

基金：

中国国家自然科学基金;

关键词：

ASYMMETRIC TOTAL-SYNTHESIS; SCALABLE SYNTHESIS; MOLECULAR-OXYGEN; ALKYL-ARYL; HYDROPEROXIDES; TRITERPENOIDS; OUABAGENIN; EFFICIENT; OXETANES; ALCOHOLS;

D O I：

10.1021/jacs.0c00363

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A concise bioinspired synthesis of Schisandra nortriterpenoid propindilactone G has been accomplished from a readily accessible steroidal lactone. Key transformations include a Breslow remote functionalization, a Suarez remote radical functionalization, a ring expansion enabled by a Wagner-Meerwein rearrangement, a stereoinversion of a tertiary alcohol, and a biomimetic transesterification/oxa-Michael addition cascade. This work also provides experimental evidence of the putative propindilactone G biosynthesis pathway.

引用

页码：5007 / 5012

页数：6

共 50 条

[1] Asymmetric total synthesis of propindilactone G
Chen, Jia-Hua (jhchen@pku.edu.cn), 1600, American Chemical Society (137):
[2] Asymmetric Total Synthesis of Propindilactone G
You, Lin
Liang, Xin-Ting
Xu, Ling-Min
Wang, Yue-Fan
Zhang, Jia-Jun
Su, Qi
Li, Yuan-He
Zhang, Bo
Yang, Shou-Liang
Chen, Jia-Hua
Yang, Zhen
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (32) : 10120 - 10123
[3] Development of Biomimetic Synthesis of Propindilactone G
Wang, Yu
Chen, Bo
He, Xubiao
Gui, Jinghan
CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (11) : 1339 - 1352
[4] Asymmetric Total Synthesis of Propindilactone G, Part 3: The Final Phase and Completion of the Synthesis
Liang, Xin-Ting
You, Lin
Li, Yuan-He
Yu, Hai-Xin
Chen, Jia-Hua
Yang, Zhen
CHEMISTRY-AN ASIAN JOURNAL, 2016, 11 (09) : 1425 - 1435
[5] Asymmetric Total Synthesis of Propindilactone G, Part 1: Initial Attempts towards the Synthesis of Schiartanes
Xu, Ling-Ming
You, Lin
Shan, Zhen-Hua
Yu, Ruo-Cheng
Zhang, Bo
Li, Yuan-He
Shi, Ying
Chen, Jia-Hua
Yang, Zhen
CHEMISTRY-AN ASIAN JOURNAL, 2016, 11 (09) : 1406 - 1413
[6] Total Synthesis of the Schisandraceae Nortriterpenoid Rubriflordilactone A
Chaubet, Guilhem
Goh, Shermin S.
Mohammad, Mujahid
Gockel, Birgit
Cordonnier, Marie-Caroline A.
Baars, Hannah
Phillips, Andrew W.
Anderson, Edward A.
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (56) : 14080 - 14089
[7] Asymmetric Total Synthesis of Propindilactone G, Part 2: Enantioselective Construction of the Fully Functionalized BCDE Ring System
Zhang, Jia-Jun
You, Lin
Wang, Yue-Fan
Li, Yuan-He
Liang, Xin-Ting
Zhang, Bo
Yang, Shou-Liang
Su, Qi
Chen, Jia-Hua
Yang, Zhen
CHEMISTRY-AN ASIAN JOURNAL, 2016, 11 (09) : 1414 - 1424
[8] 复杂天然产物(+)-Propindilactone G的不对称全合成
有机化学, 2015, (10) : 2235 - 2235
[9] Enantioselective Synthesis of the Predominant AB Ring System of the Schisandra Nortriterpenoid Natural Products
Gockel, Birgit
Goh, Shermin S.
Puttock, Emma J.
Baars, Hannah
Chaubet, Guilhem
Anderson, Edward A.
ORGANIC LETTERS, 2014, 16 (17) : 4480 - 4483
[10] BIOINSPIRED SYNTHESIS OF SILVER NANOPARTICLES
Parashar, Upendra Kumar
Saxena, Preeti S.
Srivastava, Anchal
DIGEST JOURNAL OF NANOMATERIALS AND BIOSTRUCTURES, 2009, 4 (01) : 159 - 166

← 1 2 3 4 5 →