ChemInform Abstract: Facile Access to Sterically Hindered Aryl Ketones via Carbonylative Cross-Coupling: Application to the Total Synthesis of Luteolin.

ChemInform ◽  
2011 ◽  
Vol 42 (42) ◽  
pp. no-no
Author(s):  
B. Michael O'Keefe ◽  
Nicholas Simmons ◽  
Stephen F. Martin
Keyword(s):  
Total Synthesis ◽  
Cross Coupling ◽  
Aryl Ketones ◽  
Sterically Hindered

scholarly journals Facile access to sterically hindered aryl ketones via carbonylative cross-coupling: application to the total synthesis of luteolin

Tetrahedron ◽  
2011 ◽  
Vol 67 (24) ◽  
pp. 4344-4351 ◽  
Author(s):  
B. Michael O’Keefe ◽  
Nicholas Simmons ◽  
Stephen F. Martin
Keyword(s):  
Total Synthesis ◽  
Cross Coupling ◽  
Aryl Ketones ◽  
Sterically Hindered

scholarly journals Carbonylative Cross-Coupling ofortho-Disubstituted Aryl Iodides. Convenient Synthesis of Sterically Hindered Aryl Ketones

2008 ◽  
Vol 10 (22) ◽  
pp. 5301-5304 ◽  
Author(s):  
B. Michael O’Keefe ◽  
Nicholas Simmons ◽  
Stephen F. Martin
Keyword(s):  
Cross Coupling ◽  
Aryl Iodides ◽  
Convenient Synthesis ◽  
Aryl Ketones ◽  
Sterically Hindered

The Total Synthesis of Rhabdastrellic Acid A

2018 ◽  
Author(s):  
Yaroslav Boyko ◽  
Christopher Huck ◽  
David Sarlah
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Cross Coupling ◽  
Side Chains ◽  
General Strategy ◽  
Modular Approach ◽  
Linear Sequence ◽  
Generating Sequence ◽  
First Time

<div>The first total synthesis of rhabdastrellic acid A, a highly cytotoxic isomalabaricane triterpenoid, has been accomplished in a linear sequence of 14 steps from commercial geranylacetone. The prominently strained <i>trans-syn-trans</i>-perhydrobenz[<i>e</i>]indene core characteristic of the isomalabaricanes is efficiently accessed in a selective manner for the first time through a rapid, complexity-generating sequence incorporating a reductive radical polyene cyclization, an unprecedented oxidative Rautenstrauch cycloisomerization, and umpolung 𝛼-substitution of a <i>p</i>-toluenesulfonylhydrazone with in situ reductive transposition. A late-stage cross-coupling in concert with a modular approach to polyunsaturated side chains renders this a general strategy for the synthesis of numerous family members of these synthetically challenging and hitherto inaccessible marine triterpenoids.</div>

The Merger of CF3SO2Na and Palladium Catalysis to Enable Decarboxylative Cross-Coupling for the Synthesis of Aromatic Ketones under Room Temperature

2021 ◽  
Author(s):  
Pan Xie ◽  
Cheng Xue ◽  
Cancan Wang ◽  
Dongdong Du ◽  
Sanshan Shi
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Palladium Catalysis ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Aromatic Ketones ◽  
Aryl Ketones ◽  
Oxocarboxylic Acids

A CF3SO2Na/Pd(OAc)2 co-catalyzed strategy is developed to produce aryl ketones via visible-light-induced decarboxylative cross-coupling of α-oxocarboxylic acids and aryl boronic acids. This process was perfomed under air at room temperature,...

Concise total synthesis of honokiol via Kumada cross coupling

2014 ◽  
Vol 55 (31) ◽  
pp. 4295-4297 ◽  
Author(s):  
Jada Srinivas ◽  
Parvinder Pal Singh ◽  
Yogesh Kumar Varma ◽  
Irfan Hyder ◽  
Halmuthur M. Sampath Kumar
Keyword(s):  
Total Synthesis ◽  
Cross Coupling

Total Synthesis of Hibispeptin A via Pd-Catalyzed C(sp3)–H Arylation with Sterically Hindered Aryl Iodides

2014 ◽  
Vol 16 (24) ◽  
pp. 6488-6491 ◽  
Author(s):  
Gang He ◽  
Shu-Yu Zhang ◽  
William A. Nack ◽  
Ryan Pearson ◽  
Javon Rabb-Lynch ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Aryl Iodides ◽  
Sterically Hindered

Ether Synthesis through Reductive Cross-Coupling of Ketones with Alcohols Using Me2SiHCl as both Reductant and Lewis Acid

Synlett ◽  
2017 ◽  
Vol 28 (18) ◽  
pp. 2425-2428 ◽  
Author(s):  
Bill Morandi ◽  
Yong Lee
Keyword(s):  
Functional Groups ◽  
Lewis Acid ◽  
Carbonyl Compounds ◽  
Cross Coupling ◽  
Wide Range ◽  
Direct Cross ◽  
Sterically Hindered ◽  
Polar Functional Groups ◽  
Ether Synthesis ◽  
Dialkyl Ethers

We report that a Lewis acidic silane, Me2SiHCl, can mediate the direct cross-coupling of a wide range of carbonyl compounds with alcohols to form dialkyl ethers. The reaction is operationally simple, tolerates a range of polar functional groups, can be utilized to make sterically hindered ethers, and is extendable to sulfur and nitrogen nucleo­philes.

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