Synthetic and mechanistic studies of the retro-Claisen rearrangement. 2. A facile route to medium-ring heterocycles via rearrangement of vinylcyclopropane- and cyclobutanecarboxaldehydes

1993 ◽  
Vol 58 (6) ◽  
pp. 1295-1297 ◽  
Author(s):  
Robert K. Boeckman ◽  
Matthew D. Shair ◽  
J. Ramon Vargas ◽  
Lesley A. Stolz
Keyword(s):  
Claisen Rearrangement ◽  
Mechanistic Studies ◽  
Medium Ring ◽  
Facile Route

Synthetic and Mechanistic Studies of the Aza-Retro-Claisen Rearrangement. A Facile Route to Medium Ring Nitrogen Heterocycles

2010 ◽  
Vol 12 (7) ◽  
pp. 1628-1631 ◽  
Author(s):  
Robert K. Boeckman ◽  
Nathan E. Genung ◽  
Ke Chen ◽  
Todd R. Ryder
Keyword(s):  
Claisen Rearrangement ◽  
Nitrogen Heterocycles ◽  
Mechanistic Studies ◽  
Ring Nitrogen ◽  
Medium Ring ◽  
Facile Route

Asymmetric Synthesis of a Hydroxylated Nine-membered Lactone from Tartaric Acid using the Claisen Rearrangement

2010 ◽  
Vol 63 (3) ◽  
pp. 529 ◽  
Author(s):  
Leon S.-M. Wong ◽  
Kathleen A. Turner ◽  
Jonathan M. White ◽  
Andrew B. Holmes ◽  
John H. Ryan
Keyword(s):  
Natural Products ◽  
Asymmetric Synthesis ◽  
Tartaric Acid ◽  
Claisen Rearrangement ◽  
Cyclic Carbonate ◽  
Thermal Elimination ◽  
Ketene Acetal ◽  
Medium Ring

The synthesis of a hydroxylated vinyl-appended lactone, in five synthetic steps from tartaric acid, is reported. The C2-symmetrical bis-vinyl diol 12 was converted into the ketene acetal 14 via methylenation of the cyclic carbonate 13 or thermal elimination of benzeneselenenic acid from the selenoxide 17. In both cases, the in situ generated ketene acetal 14 underwent spontaneous Claisen rearrangement to give the nine-membered lactone (+)-15. Lactones of this type are potentially advanced precursors to simplified eleutherobin analogues or other medium-ring lactone natural products.

ChemInform Abstract: Synthesis of Fused Bicyclic Medium-Ring Lactones via Claisen Rearrangement.

ChemInform ◽  
2010 ◽  
Vol 31 (31) ◽  
pp. no-no
Author(s):  
Jonathan W. Burton ◽  
Paul T. O'Sullivan ◽  
Edward A. Anderson ◽  
Ian Collins ◽  
Andrew B. Holmes
Keyword(s):  
Claisen Rearrangement ◽  
Medium Ring

Synthesis of medium-ring lactones via tandem methylenation/Claisen rearrangement of cyclic carbonates

Tetrahedron ◽  
2002 ◽  
Vol 58 (10) ◽  
pp. 1943-1971 ◽  
Author(s):  
Edward A Anderson ◽  
James E.P Davidson ◽  
Justin R Harrison ◽  
Paul T O'Sullivan ◽  
Jonathan W Burton ◽  
...  
Keyword(s):  
Claisen Rearrangement ◽  
Cyclic Carbonates ◽  
Medium Ring

The Claisen rearrangement approach to fused bicyclic medium-ring oxacycles

2008 ◽  
Vol 6 (4) ◽  
pp. 693 ◽  
Author(s):  
Jonathan W. Burton ◽  
Edward A. Anderson ◽  
Paul T. O'Sullivan ◽  
Ian Collins ◽  
John E. Davies ◽  
...  
Keyword(s):  
Claisen Rearrangement ◽  
Medium Ring

Development of the Claisen Rearrangement/Organocatalytic Diels-Alder Approach for the Synthesis of Eunicellins

2014 ◽  
Vol 67 (9) ◽  
pp. 1189 ◽  
Author(s):  
Joel F. Hooper ◽  
Jonathan M. White ◽  
Andrew B. Holmes
Keyword(s):  
Natural Products ◽  
Claisen Rearrangement ◽  
Cycloaddition Reaction ◽  
Diels Alder ◽  
Powerful Method ◽  
Medium Ring

The intramolecular Diels-Alder approach to synthesizing eunicellins has proved to be a powerful method for the synthesis of this class of natural products. The key to the success of this strategy is control over the endo/exo selectivity of the cycloaddition reaction, which we have addressed through an organocatalytic reaction employing the MacMillan imidazolidinone catalyst. This approach has been further developed to address the issue of functionality at the C8 position, and a novel scalable method for the extension of the medium-ring lactone has been developed.

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