First Total Synthesis of Arylnaphthalene Lignan Oleraisoindole A

被引：0

作者：

Zhou, Weizeng ^{[1
]}

Chen, Chenglong ^{[1
]}

Sun, Shuyu ^{[1
]}

Chu, Shanpeng ^{[1
]}

Li, Mengying ^{[1
]}

Xia, Yamu ^{[1
]}

机构：

[1] Qingdao Univ Sci & Technol, Dept Chem Engn, Qingdao 266042, Peoples R China

来源：

INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY | 2020年 / 30卷 / 01期

基金：

中国国家自然科学基金;

关键词：

Oleraisoindole A; Arylnaphthalene lignans; Electrocyclic reaction; Total synthesis; Lignans; OVERCROWDED MOLECULES; DERIVATIVES;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

First total synthesis of arylnaphthalene lignan Oleraisoindole A, isolated from Hyoscyamus niger, has been reported here. Oleraisoindole A has been known for its certain inhibitory effects on the growth of breast tumor cells and white blood cells. Therefore, we design a 13-step strategy to synthesize Oleraisoindole A, involving hydrolysis, dehydration, acylation, and Pd/C catalyzed hydrogenation. The structures of all compounds were confirmed by H-1 nuclear magnetic resonance (NMR), C-13 NMR, and high-resolution mass spectra. [GRAPHICS]

引用

页码：107 / 113

页数：7

共 50 条

[41] Discovery of selective filoviral inhibitors through phenotypic screening of an arylnaphthalene lignan library
Lindstrom, Aaron
Petrov, Dino
Davisson, Vincent
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
[42] 1-arylnaphthalene lignan: A novel scaffold for type 5 phosphodiesterase inhibitor
Ukita, T
Nakamura, Y
Kubo, A
Yamamoto, Y
Takahashi, M
Kotera, J
Ikeo, T
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (07) : 1293 - 1305
[43] Towards the Total Synthesis of Schisandrene: Stereoselective Synthesis of the Dibenzocyclooctadiene Lignan Core
Venkanna, Arramshetti
Poornima, Borra
Siva, Bandi
Babu, B. Hari
Babu, K. Suresh
SYNLETT, 2018, 29 (07) : 908 - 911
[44] SYNTHESIS OF 2 ARYLNAPHTHALENE LIGNANS
GONZALEZ, AG
PEREZ, JP
TRUJILLO, JM
TETRAHEDRON, 1978, 34 (07) : 1011 - 1013
[45] SOLID-STATE FLUORODENSITOMETRIC QUANTITATION OF ARYLNAPHTHALENE LIGNAN LACTONES OF CLEISTANTHUS-COLLINUS
ANNAPOORANI, KS
DAMODARAN, C
SEKHARAN, PC
JOURNAL OF CHROMATOGRAPHY, 1984, 303 (01): : 296 - 305
[46] ARYLNAPHTHALENE LIGNANS - SYNTHESIS OF HELIOXANTHIN
HOLMES, TL
STEVENSO.R
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (11): : 2091 - &
[47] Efficient Syntheses of 1-Arylnaphthalene Lignan Lactones and Related Compounds from Cyanohydrins
J Org Chem, 14 (4585):
[48] STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-SAMIN, THE GENERAL FUROFURAN LIGNAN PRECURSOR
MAITI, G
ADHIKARI, S
ROY, SC
TETRAHEDRON LETTERS, 1994, 35 (36) : 6731 - 6732
[49] A new arylnaphthalene type lignan from Cordia rufescens A. DC. (Boraginaceae)
da Silvaa, SAS
Souto, AL
Agra, MD
da-Cunha, EVL
Barbosa, JM
da Silva, MS
Braz Filho, R
ARKIVOC, 2004, : 54 - 58
[50] Axial Chirality and Antiviral Activity Evaluation of Arylnaphthalene Lignan Glycosides from Justicia procumbens
Zhao, Yang
Tsang, Nga Yi
Xu, Xin-Ya
Zhao, Chen-Liang
Ku, Chuen-Fai
Li, Wan-Fei
Zhu, Yu
Liu, Kang-Lun
Rong, Lijun
Zhang, Hong-Jie
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (08)

← 1 2 3 4 5 →