Synthesis of Tanshinone IIA and Related Terpenes via a C-H Functionalization Strategy

被引：1

作者：

Tucker, Nathan ^{[1
]}

Britt, Liam H. ^{[1
]}

Grover, Huck K. ^{[1
]}

机构：

[1] Mem Univ Newfoundland, Dept Chem, St John, NF A1B 3X7, Canada

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 34期

基金：

加拿大自然科学与工程研究理事会;

关键词：

DIRECT ORTHO-ARYLATION; ARYL CARBOXYLIC-ACIDS; BENZOIC-ACIDS; BOND ACTIVATIONS; PI;

D O I：

10.1021/acs.orglett.4c02438

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of tanshinone IIA and related bioactive diterpenes isolated from the Chinese plant Salvia miltiorrhiza was completed from a common tetralin building block. The synthetic route highlights a 3,4-disubstituted furan synthesis and various regioselective C-H functionalization reactions, including a Pd catalyzed iodination and an Ir catalyzed borylation, along with an intramolecular stanna-Brook type reaction to construct the ortho-quninone ring of the target molecule.

引用

页码：7134 / 7138

页数：5

共 50 条

[11] C-H Functionalization in organic synthesis
Davies, Huw M. L.
Du Bois, Justin
Yu, Jin-Quan
CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) : 1855 - 1856
[12] C-H Functionalization Logic Enables Synthesis of (+)-Hongoquercin A and Related Compounds
Rosen, Brandon R.
Simke, Leah R.
Thuy-Boun, Peter S.
Dixon, Darryl D.
Yu, Jin-Quan
Baran, Phil S.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (28) : 7317 - 7320
[13] Progress in the Synthesis of Primary Anilines via C-H Bond Functionalization
Xu, Linlin
Xu, Hui
Lin, Haixia
Dai, Huixiong
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (08) : 1940 - 1948
[14] Recent Advances on Benzofuranones: Synthesis and Transformation via C-H Functionalization
Tang, Zhi
Tong, Zhou
Qiu, Renhua
Yin, Shuang-Feng
Kambe, Nobuaki
SYNTHESIS-STUTTGART, 2021, 53 (18): : 3193 - 3210
[15] Macrocyclization via C-H functionalization: a new paradigm in macrocycle synthesis
Sengupta, Saumitra
Mehta, Goverdhan
ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (10) : 1851 - 1876
[16] Synthesis of amino acids via catalytic C-H functionalization of alcohols
Stateman, Leah
Wappes, Ethan
Nakafuku, Kohki
Nagib, David
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
[17] Oxindole Synthesis via Palladium-catalyzed C-H Functionalization
Magano, Javier
Kiser, E. Jason
Shine, Russell J.
Chen, Michael H.
Hughes, David
ORGANIC SYNTHESES, 2013, 90 : 74 - +
[18] Heterocycle biosynthesis via C-H functionalization
Hahn, Frank
NATURE CATALYSIS, 2018, 1 (12): : 905 - 906
[19] Synthesis of rhazinicine by a metal-catalyzed C-H bond functionalization strategy
Beck, Elizabeth M.
Hatley, Richard
Gaunt, Matthew J.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (16) : 3004 - 3007
[20] Electrochemical oxidative site-selective direct C-H activation of tanshinone IIA
Zhang, Jingyi
Han, Shan
Lu, Siao
Li, Minghan
Gao, Zixun
Zheng, Linyu
Feng, Yulin
Lu, Fangling
ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (45) : 8838 - 8842

← 1 2 3 4 5 →