Regio- and Diastereo-Selective Biomimetic Synthesis of (±)-ε-Viniferin by NIS and Resveratrol

被引：3

作者：

D'Orsi, Rosarita ^{[1
]}

Morrongiello, Francesca ^{[1
]}

Laurita, Teresa ^{[1
]}

Funicello, Maria ^{[1
]}

Lupattelli, Paolo ^{[1
]}

Chiummiento, Lucia ^{[1
]}

机构：

[1] Univ Basilicata, Dept Sci, Via Dellateneo Lucano 10, I-85100 Potenza, Italy

来源：

CHEMISTRYSELECT | 2021年 / 6卷 / 27期

关键词：

biomimetic synthesis; epsilon-viniferin; halogenation; radical reaction; resveratrol; BIOACTIVE BENZOFURAN DERIVATIVES; PERMETHYLATED ANIGOPREISSIN; AMURENSIN-H; CONSTITUENTS; HALIDES; AGENTS;

D O I：

10.1002/slct.202101678

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this work, we describe the synthesis of (+/-)-permethylated-epsilon-viniferin from resveratrol by successive iodination, methylation and dehalogenation reactions. Iodination reaction by N-iodosuccinimide (NIS) was studied to optimize and confirm a proposed radical mechanism. Switching to acetyl protecting group, a new straightforward regio- and diastereo-selective biomimetic synthesis of (+/-)-epsilon-viniferin was obtained. Permethylated and free epsilon-viniferin were isolated up to 20 %yield.

引用

页码：6863 / 6866

页数：4

共 32 条

[1] PdCl2-catalyzed reduction of organic halides by triethylsilane
Boukherroub, R
Chatgilialoglu, C
Manuel, G
[J]. ORGANOMETALLICS, 1996, 15 (05) : 1508 - 1510
[2] Bu3SnH mediated oxidative radical cyclisations:: synthesis of 6H-benzo[c]chromen-6-ones
Bowman, WR
Mann, E
Parr, J
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (17): : 2991 - 2999
[3] Phytochemical Investigation of the Constituents Derived from the Australian Plant Macropidia fuliginosa
Brkljaca, Robert
White, Jonathan M.
Urban, Sylvia
[J]. JOURNAL OF NATURAL PRODUCTS, 2015, 78 (07): : 1600 - 1608
[4] A practical palladium catalyzed dehalogenation of aryl halides and α-haloketones
Chen, Jingbo
Zhang, Yushun
Yang, Liquan
Zhang, Xiang
Liu, Jianping
Li, Liang
Zhang, Hongbin
[J]. TETRAHEDRON, 2007, 63 (20) : 4266 - 4270
[5] Synthetic approaches to natural products containing 2,3-dihydrobenzofuran skeleton
Chen, Zhuang
Pitchakuntla, Mallesham
Jia, Yanxing
[J]. NATURAL PRODUCT REPORTS, 2019, 36 (04) : 666 - 690
[6] Last Decade of Unconventional Methodologies for the Synthesis of Substituted Benzofurans
Chiummiento, Lucia
D'Orsi, Rosarita
Funicello, Maria
Lupattelli, Paolo
[J]. MOLECULES, 2020, 25 (10):
[7] Concise Total Synthesis of Permethylated Anigopreissin A, a New Benzofuryl Resveratrol Dimer
Chiummiento, Lucia
Funicello, Maria
Lopardo, Maria Teresa
Lupattelli, Paolo
Choppin, Sabine
Colobert, Francoise
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (01) : 188 - 192
[8] Permethylated Anigopreissin A inhibits human hepatoma cell proliferation by mitochondria-induced apoptosis
Convertini, Paolo
Tramutola, Francesco
Iacobazzi, Vito
Lupattelli, Paolo
Chiummiento, Lucia
Infantino, Vittoria
[J]. CHEMICO-BIOLOGICAL INTERACTIONS, 2015, 237 : 1 - 8
[9] Structural Insights into the TES/TFA Reduction of Differently Substituted Benzofurans: Dihydrobenzofurans or Bibenzyls?
D'Orsi, Rosarita
Caivano, Ilaria
Funicello, Maria
Lupattelli, Paolo
Chiummiento, Lucia
[J]. SYNLETT, 2021, 32 (01) : 63 - 68
[10] DOrsi R., CHEMISTRYSELECT, V2021, P6863

← 1 2 3 4 →