Total synthesis of rodgersinol: a survey of the Cu(II)-mediated coupling of ortho-substituted phenols

被引：6

作者：

Jung, Jong-Wha ^{[1
]}

Jang, Jaebong ^{[1
]}

Seo, Seung-Yong ^{[2
]}

Jung, Jae-Kyung ^{[3
]}

Suh, Young-Ger ^{[1
]}

机构：

[1] Seoul Natl Univ, Coll Pharm, Seoul 151742, South Korea

[2] Woosuk Univ, Coll Pharm, Wonju 565701, South Korea

[3] Chungbuk Natl Univ, Coll Pharm, Cheongju 361763, South Korea

来源：

TETRAHEDRON | 2010年 / 66卷 / 34期

关键词：

ALPHA-ARYLPROPANOIC ACIDS; DIARYL ETHER SYNTHESIS; ASYMMETRIC DIHYDROXYLATION; CONCISE SYNTHESIS; COPPER; DERIVATIVES; CATALYSTS; EPOXIDES; AGENTS; ROUTE;

D O I：

10.1016/j.tet.2010.06.048

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Full details of studies directed toward the total synthesis of both enantiomers of rodgersinol are described. The key parts of our synthetic route to rodgersinol included the Cu(II)-mediated coupling of an arylboronic acid with an ortho-alkyl substituted phenol and regio- and stereoselective construction of the hydroxypropyl substituent. which avoided tedious protection/deprotection sequence. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：6826 / 6831

页数：6

共 50 条

[41] SYNTHESIS OF ORTHO-SUBSTITUTED ARENE CHROMIUM TRICARBONYLS
BARBIERI, G
BENASSI, R
SYNTHESIS AND REACTIVITY IN INORGANIC AND METAL-ORGANIC CHEMISTRY, 1974, 4 (06): : 545 - 547
[42] METAL-LIGAND STABILITY CONSTANTS OF SOME ORTHO-SUBSTITUTED PHENOLS
JABALPURWALA, KE
VENKATACHALAM, KA
KABADI, MB
JOURNAL OF INORGANIC & NUCLEAR CHEMISTRY, 1964, 26 (06): : 1027 - 1043
[43] Action of Tyrosinase on Ortho-Substituted Phenols: Possible Influence on Browning and Melanogenesis
del Mar Garcia-Molina, Maria
Luis Munoz-Munoz, Jose
Garcia-Molina, Francisco
Antonio Garcia-Ruiz, Pedro
Garcia-Canovas, Francisco
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2012, 60 (25) : 6447 - 6453
[44] SYNTHESIS OF ORTHO-SUBSTITUTED BENZONITRILES BY NITRO DISPLACEMENT
BECK, JR
SOBCZAK, RL
SUHR, RG
YAHNER, JA
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (13): : 1839 - 1841
[45] SYNTHESIS AND PHARMACOLOGICAL ACTIONS OF ORTHO-SUBSTITUTED PHENETHYLHYDRAZINES
SCHUMANN, EL
GREIG, ME
SEAY, PH
HEINZELMAN, RV
JOURNAL OF MEDICINAL & PHARMACEUTICAL CHEMISTRY, 1961, 3 (03): : 567 - &
[46] Synthesis and antimitotic properties of ortho-substituted polymethoxydiarylazolopyrimidines
Chernyshova, Natalia B.
Tsyganov, Dmitry V.
Khrustalev, Victor N.
Raihstat, Mikhail M.
Konyushkin, Leonid D.
Semenov, Roman V.
Semenova, Marina N.
Semenov, Victor V.
ARKIVOC, 2017, : 151 - 165
[47] SYNTHESIS OF ORTHO-SUBSTITUTED PHOSPHINYLPHENOL, PHOSPHINYLMETHYLPHENOL AND PHOSPHINYLETHYLPHENOL
BONDARENKO, NA
TSVETKOV, EN
MATROSOV, EI
KABACHNIK, MI
BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1979, 28 (02): : 399 - 403
[48] Coupling of Fischer carbene complexes with ortho-substituted phenylacetylene derivatives
Jackson, TJ
Herndon, JW
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 214 : 303 - ORGN
[49] HYDROGEN-BONDING INTERACTIONS OF ALIPHATIC-AMINES WITH ORTHO-SUBSTITUTED PHENOLS
FARAH, L
GILES, G
WILSON, D
OHNO, A
SCOTT, RM
JOURNAL OF PHYSICAL CHEMISTRY, 1979, 83 (19): : 2455 - 2458
[50] SYNTHESIS OF FORMAZANS FROM ORTHO-SUBSTITUTED ARYLIDENE ARYLHYDRAZINES
HEGARTY, AF
SCOTT, FL
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (23): : 2507 - &

← 1 2 3 4 5 →