Diastereoselective and enantioselective preparation of nor-mevaldic acid surrogates through desymmetrisation methodology. Enantioselective synthesis of (+) and (−) nor-mevalonic lactones

Abstract

Diastereoselective and enantioselective preparation of nor-mevaldic acid surrogates through desymmetrisation methodology. Enantioselective synthesis of (+) and (-) normevalonic lactones Please cite this article as: Botubol-Ares JM, Durán-Peña MJ, Hernández-Galán R, Collado IG, Harwood LM, Macías-Sánchez AJ, Diastereoselective and enantioselective preparation of nor-mevaldic acid surrogates through desymmetrisation methodology. Enantioselective synthesis of (+) and (-) normevalonic lactones, Tetrahedron (2015), Abstract Diastereoselective and enantioselective preparation of nor-mevaldic acid surrogates through desymmetrisation methodology. Enantioselective synthesis of (+) and (-) nor-mevalonic lactones.

Navigating around Patented Routes by Preserving Specific Motifs along Computer-Planned Retrosynthetic Pathways

“…Similarly, in (D) the ester motif appears intact but in reality is not preserved during lactonization reaction. 11 characteristics: (1) it preserves the not-to-be-altered bonds along entire pathways it identifies; (2) it can preserve motifs that are disjoint in the target-in such a case, at a given generation, more than one bond set Bðs i Þ is not empty, meaning that the motifs are split between different synthons; and (3) it can be implemented to prevent either complete bond disconnections or changes in bond order (the latter, by adding bond-order labels to atom labels). For the pseudocode of the algorithm, see Supplemental Information Section S3.…”

“…For instance, in (C), the red-colored double bond C 2 =C 3 might seem to be preserved, but in reality it is disconnected during olefin metathesis,10 as indicated by the atom numbers. Similarly, in (D) the ester motif appears intact but in reality is not preserved during lactonization reaction 11.…”

General Synthesis of meso-1,4-Dialdehydes and Their Application in Ir-Catalyzed Asymmetric Tishchenko Reactions

“…In the last four decades, 1,5-prochiral, − 1,5- meso -, − 1,6-prochiral, − 1,6- meso -, − and 1,7- meso -dialdehydes ,,,− , have been synthesized (Figure ) using various methods, including the Swern oxidation of the corresponding diols, − ,,, pyridinium-chlorochromate oxidation, tetrapropylammonium-perruthenate oxidation, oxidative cleavage of diols using H 5 IO 6 ,,,, or NaIO 4 , and ozonolysis of alkenes. ,,, The purification of 1,7- meso -dialdehydes by column chromatography on silica gel has also been reported, albeit that these dialdehydes are generally used without purification. In 1,5-dialdehydes, where the distance between the two formyl groups is shorter, cyclic hydrates are formed .…”