Total Synthesis of Gramistilbenoids A, B, and C

被引：8

作者：

Harmalkar, Dipesh S. ^{[1
]}

Lu, Qili ^{[1
]}

Lee, Kyeong ^{[1
]}

机构：

[1] Dongguk Univ Seoul, Coll Pharm, Goyang 10326, South Korea

来源：

JOURNAL OF NATURAL PRODUCTS | 2018年 / 81卷 / 04期

基金：

新加坡国家研究基金会;

关键词：

STILBENE DERIVATIVES; POLYGONUM-MULTIFLORUM; ARUNDINA-GRAMINIFOLIA; PHENOLIC-COMPOUNDS; RESVERATROL; TARGETS; DIPHENYLETHYLENES; ANTIOXIDANT; INHIBITION; PREVENTION;

D O I：

10.1021/acs.jnatprod.7b00865

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

Stilbenes are biologically active metabolites of plants that have the potential to attenuate a broad range of human diseases. Gramistilbenoids are a class of natural products with a stilbene skeleton, isolated from the bamboo orchid (Arundina graminifolia), and with significant cytotoxicity against cancer cell lines (NB4, A549, SHSYSY, PC3, and MCF7). These are the first identified naturally occurring diphenylethylenes to possess a hydroxyethyl unit. However, some of these compounds are not abundant in nature, and thus, their synthesis is advantageous. This paper reports the first synthesis of gramistilbenoids A (1), B (2), and C (3), with overall yields of 10, 2, and 8% respectively. These natural products were synthesized using key reactions, such as Horner-Wadsworth-Emmons olefination, Stille coupling, and hydroboration oxidation.

引用

页码：798 / 805

页数：8

共 50 条

[21] Total synthesis of desoxycyclomarin C and the cyclomarazines A and B
Barbie, Philipp
Kazmaier, Uli
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (25) : 6055 - 6064
[22] Biomimetic Total Synthesis of Gracilioethers B and C
Norris, Matthew D.
Perkins, Michael V.
Sorensen, Erik J.
ORGANIC LETTERS, 2015, 17 (03) : 668 - 671
[23] Total synthesis of rutamycin B and oligomycin C
Panek, JS
Jain, NF
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (08): : 2747 - 2756
[24] Total Synthesis of Mniopetals A, B, C and D
Weihrather, Joachim
Jauch, Johann
SYNLETT, 2013, 24 (11) : 1410 - 1414
[25] Concise Total Synthesis of Herqulines B and C
He, Chi
Stratton, Thomas P.
Baran, Phil S.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (01) : 29 - 32
[26] Asymmetric Total Synthesis of Oxazolomycins B and C
Song, Yeonghun
Kim, Jae Hyun
Chan Kim, Young
Kim, Sanghee
CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (41) : 10731 - 10736
[27] Total synthesis of cyrneines A–B and glaucopine C
Guo-Jie Wu
Yuan-He Zhang
Dong-Xing Tan
Fu-She Han
Nature Communications, 9
[28] Concise Total Synthesis of Helicascolides A, B, and C
Yadav, Jhillu Singh
Reddy, Anugu Bal
Shankar, Kattela Shiva
SYNTHESIS-STUTTGART, 2013, 45 (08): : 1034 - 1038
[29] The total synthesis of coleophomones B, C, and D
Nicolaou, K.C.
Montagnon, Tamsyn
Vassilikogiannakis, Georgios
Mathison, Casey J. N.
Journal of the American Chemical Society, 2005, 127 (24): : 8872 - 8888
[30] Stereoselective Total Synthesis of (-)-Isocladospolide B and Cladospolide B and C
Yadav, J. S.
Mandal, S. S.
SYNLETT, 2011, (19) : 2803 - 2806

← 1 2 3 4 5 →