A concise, stereocontrolled total synthesis of rippertenol
The first total synthesis of the unique terpene rippertenol, a molecule with dense stereochemical complexity arrayed on a compact framework largely devoid of functional groups, is described. Key elements include orchestrated and unique applications of aldol condensations, Diels-Alder chemistry, and a ring expansion to advance a chiral starting material containing a single chiral center into the final target in a concise and diastereocontrolled manner.
Snyder, Scott A.,Wespe, Daniel A.,Von Hof, J. Marian
supporting information; experimental part
p. 8850 - 8853
(2011/08/04)
Abnormal Ito-Saegusa oxidation of TIPS enol ether assisted by a hydroxy group on a side chain
Although Ito-Saegusa oxidation gives defined α,β-unsaturated ketones from silyl enol ether of ketones controlled by the position of the sp2 carbon of the silyl enol ether, the formation of a regioisomeric product that was oxidized abnormally wa
Hiraoka, Shiharu,Harada, Shinji,Nishida, Atsushi
experimental part
p. 3079 - 3082
(2011/06/26)
Synthesis of optically active cyclohexenol derivatives via enzyme catalyzed ester hydrolysis of 4-acetoxy-3-methyl-2-cyclohexenone
The optically active cyclohexenol derivatives 9a-9d, and 10a-10c are synthesized from (-)-6, which is obtained by enzymatic ester hydrolysis of racemic 8. Attempts towards the synthesis of the taxane skeleton are described.
Polla, Magnus,Frejd, Torbjoern
p. 5883 - 5894
(2007/10/02)
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