79691-11-5Relevant articles and documents
Stereocontrolled functionalization of the diene system of compactin
Senanayake, Chris H.,Bill, Timothy J.,DiMichele, Lisa M.,Chen, Cheng Y.,Larsen, Robert D.,Verhoeven, Thomas R.,Reider, Paul J.
, p. 6021 - 6024 (2007/10/02)
A facile regio- and stereo selective γ-functionlization of the 1,3-diene system of compactin via the key dienone 3 is described.
Remote Diastereoselection in the Asymmetric Total Synthesis of Mevinolin
Wovkulich, P. M.,Tang, P. C.,Chadha, N. K.,Batcho, A. D.,Barrish, J. C.,Uskokovic, M. R.
, p. 2596 - 2599 (2007/10/02)
The asymmetric total synthesis of mevinolin (1a) is described.The key diastereoselective processes used to parlay the lone stereogenic center of asymmetrically produced (S)-pulegone (2a) to mevinolin include orthoester-Claisen rearrangement of 2d to 3a, stereoselective iodolactonization of 3e to 4, Eschenmoser-Claisen rearrangement of 6 to 7a, stereoselective intramolecular ene reaction of 7b to 8, and a highly diastereoselective cyclocondesation of aldehyde 10 with Danishefsky's diene.The cyclocondensation reaction was found to be quite sensitive to the reactionconditions in which the use of TiCl4 produced a 90:10 mixture of 11/12 while MgBr2 gave a 22:78 mixture
Reductive Transformation and Cyclopropanation of Mevinolin (α-Methylcompactin). Generation of Chirality in the 1,4-Hydrostannation of a Cyclic Diene
Kuo, C. H.,Patchett, A. A.,Wendler, N. L.
, p. 1991 - 1998 (2007/10/02)
Conversion of mevinolin by direct reductive procedures as well as by indirect chemical transformations has permitted the preparation of the various di- and tetrahydro derivatives.Cyclopropanation of mevinolin and its derivatives has furnished mono- and di