Synthetic photochemistry. Part 44. Total synthesis of ceroplastol II and albolic acid, 5-8-5-membered tricyclic sesterterpenoid insect wax constituents, via stereocontrolled silyloxy-Cope rearrangement with a normally disfavoured transition state

1989 ◽  
pp. 165 ◽  
Author(s):  
Nobuo Kato ◽  
Hitoshi Takeshita ◽  
Hideo Kataoka ◽  
Shoji Ohbuchi ◽  
Shinya Tanaka
Keyword(s):  
Transition State ◽  
Total Synthesis ◽  
Cope Rearrangement

scholarly journals Transient [3,3] Cope rearrangement of 3,3-dicyano-1,5-dienes: computational analysis and 2-step synthesis of arylcycloheptanes

2018 ◽  
Vol 9 (46) ◽  
pp. 8760-8764 ◽  
Author(s):  
Ehsan Fereyduni ◽  
Jacob N. Sanders ◽  
Gabriel Gonzalez ◽  
K. N. Houk ◽  
Alexander J. Grenning
Keyword(s):  
Transition State ◽  
Computational Analysis ◽  
Cope Rearrangement ◽  
State Analysis

Unexpectedly mild [3,3] rearrangement computed transition state analysis, regio- and diastereoselecitve transformations multicomponent couplings, convergent 2-step arylcycloheptene synthesis.

scholarly journals Aza-Cope Rearrangement−Mannich Cyclizations for the Formation of Complex Tricyclic Amines:  Stereocontrolled Total Synthesis of (±)-Gelsemine

2005 ◽  
Vol 127 (51) ◽  
pp. 18046-18053 ◽  
Author(s):  
William G. Earley ◽  
Jon E. Jacobsen ◽  
Andrew Madin ◽  
G. Patrick Meier ◽  
Christopher J. O'Donnell ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Cope Rearrangement

Anion-Accelerated Aromatic Oxy-Cope Rearrangement in Geranylation/Nerylation of Xanthone: Stereochemical Insights and Synthesis of Fuscaxanthone F

Synlett ◽  
2020 ◽  
Vol 31 (14) ◽  
pp. 1378-1383
Author(s):  
Takashi Matsumoto ◽  
Yuuki Fujimoto ◽  
Kanae Takahashi ◽  
Ryouma Kobayashi ◽  
Haruhiko Fukaya ◽  
...  
Keyword(s):  
Transition State ◽  
Side Chain ◽  
Cope Rearrangement ◽  
State Structure ◽  
Transition State Structure

An efficient installation of a 3,7-dimethylocta-2,6-dien-1-yl (geranyl or neryl) side chain at the C(1) position of a xanthone core by utilizing an anion-accelerated aromatic oxy-Cope rearrangement is described. Experiments revealed that this uncommon rearrangement takes place in a stereospecific manner through a chair-like transition-state structure. An application to the syntheses of the natural xanthone fuscaxanthone F, possessing a geranyl side chain, and its neryl analogue is also described.

Asymmetric cyclopropanation of chiral (1-phosphoryl)vinyl sulfoxides: A new approach to constrained analogs of biologically active compounds

2005 ◽  
Vol 77 (12) ◽  
pp. 2091-2098 ◽  
Author(s):  
Marian Mikołajczyk
Keyword(s):  
Transition State ◽  
Total Synthesis ◽  
Bioactive Compounds ◽  
Theoretical Calculations ◽  
Experimental Results ◽  
Biologically Active ◽  
Active Compounds ◽  
New Approach ◽  
Cyclic Analog ◽  
Asymmetric Cyclopropanation

This account outlines the results obtained in the author's laboratory on the asymmetric cyclopropanation of enantiopure 1-phosphorylvinyl p-tolyl sulfoxides with sulfur ylides and diazoalkanes. Based on experimental results and theoretical calculations, the transition-state model for asymmetric cyclopropanation is proposed. A great synthetic value of the reaction investigated is exemplified by the total synthesis of constrained analogs of bioactive compounds, namely, enantiopure cyclic analog of phaclofen and cyclopropylphosphonate analogs of nucleotides.

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