A new method of phosphorus-selenium bond cleavage. Stereocontrolled synthesis of P-chiral phosphoric-trifluoroacetic anhydrides

1992 ◽  
Vol 57 (22) ◽  
pp. 6057-6060 ◽  
Author(s):  
Lucyna A. Wozniak ◽  
Bozenna Krzyzanowska ◽  
Wojciech J. Stec
Keyword(s):  
Bond Cleavage ◽  
New Method ◽  
Stereocontrolled Synthesis

scholarly journals Total Synthesis of (–)-Picrotoxinin

2019 ◽  
Author(s):  
Steven W. M. Crossley ◽  
Guanghu Tong ◽  
Michael J. Lambrecht ◽  
Hannah E. Burdge ◽  
Ryan Shenvi
Keyword(s):  
Total Synthesis ◽  
Bond Cleavage ◽  
Stereocontrolled Synthesis

We report a concise, stereocontrolled synthesis of the neurotoxic sesquiterpenoid, (–)-picrotoxinin (<b>1</b>, PXN). The brevity of the route owes to regio- and stereoselective formation of the [4.3.0] bicyclic core by incorporation of a symmetrizing geminal dimethyl group at C5. A series of strong C–C and C–H bond oxidations convert the C5 <i>gem</i>-dimethyl group to the C15 lactone of PXN. This counterintuitive strategy features the first example of demethylation (C–C bond cleavage) in total synthesis.<br>

ChemInform Abstract: A New Method for Radical Generation: Reductive C-Se or C-S Bond Cleavage of Cyclic Onium Salts.

ChemInform ◽  
2010 ◽  
Vol 22 (7) ◽  
pp. no-no
Author(s):  
T. KATAOKA ◽  
K. TSUTSUMI ◽  
K. KANO ◽  
K. MORI ◽  
M. MIYAKE ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
New Method ◽  
Onium Salts ◽  
Radical Generation

A Ruthenium-Catalyzed Reaction of Aromatic Ketones with Arylboronates:  A New Method for the Arylation of Aromatic Compounds via C−H Bond Cleavage

2003 ◽  
Vol 125 (7) ◽  
pp. 1698-1699 ◽  
Author(s):  
Fumitoshi Kakiuchi ◽  
Shintaro Kan ◽  
Kimitaka Igi ◽  
Naoto Chatani ◽  
Shinji Murai
Keyword(s):  
Aromatic Compounds ◽  
Bond Cleavage ◽  
New Method ◽  
Aromatic Ketones
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