scholarly journals A new synthetic route to methyl (-)-shikimate by asymmetric diels-alder reaction of (S)s-3-(2-pyridylsulfinyl)acrylate.

1988 ◽  
Vol 36 (8) ◽  
pp. 3213-3215 ◽  
Author(s):  
Tamiko Takahashi ◽  
Toshie Namiki ◽  
Yoshio Takeuchi ◽  
Toru Koizumi
2011 ◽  
Vol 89 (12) ◽  
pp. 1457-1468 ◽  
Author(s):  
Bryan Hill ◽  
Robert Jordan ◽  
Yang Qu ◽  
Abdeljalil Assoud ◽  
Russell Rodrigo

Homochiral AB segments for (+)- and (–)-pillaromycinone were prepared in 11 steps from 2-acetylfuran. The synthesis featured an intramolecular Diels–Alder reaction of a 2,5-disubstituted furan and a hydroxyl-directed homogeneous hydrogenation of the tetrasubstituted alkene double bond of two enones. The CD segment was attached by a modified Staunton–Weinreb annulation to produce the desired homochiral tetracycle 21c related to (+)-pillaromycinone. An unusual acetonide migration enabled the synthesis of a tetracyclic model for premithramycinone.


2011 ◽  
Vol 89 (3) ◽  
pp. 409-414 ◽  
Author(s):  
Nick Henry Werstiuk ◽  
Wojciech Sokol

Aimed at predicting relative reactivities, density functional theory (DFT) calculations were carried out on a series of Diels–Alder reactions involving silylvinyl derivatives reacting with cyclopentadiene as part of a synthetic research project. Using three reactions for which experimental rate data are available to calibrate our calculations, we computationally pinpointed the best synthetic route to bicyclo[2.2.1]hept-5-ene-2,2-diylbis(trimethylsilane) (1). The synthesis begins with the Diels–Alder reaction of cyclopentadiene (2) with commercially available (1-bromovinyl)trimethylsilane (6).


ChemInform ◽  
2010 ◽  
Vol 24 (16) ◽  
pp. no-no
Author(s):  
G. A. TOLSTIKOV ◽  
E. E. SHUL'TS ◽  
T. SH. MUKHAMETYANOVA ◽  
V. S. SULTANOVA ◽  
L. V. SPIRIKHIN

1996 ◽  
Vol 37 (7) ◽  
pp. 999-1002 ◽  
Author(s):  
Michael Schmittel ◽  
Marc Strittmatter ◽  
Karl Vollmann ◽  
Susanne Kiau

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