Titanium-Mediated Diastereoselective Formation of (E)- or (Z)-2-Substituted 1-Vinylcyclopropanols: Scope and Limitation, Applications

Synthesis of 2-Alkenyl-Tethered Anilines

“…16 Reduction of the resulting ester 15 to alcohol 16 , 16 followed by a two-step sequence of mesylation and hydride reduction, afforded the aryl bromide 17 . 17 The aryl bromide 17 was then subjected to Hartwig’s C–N coupling method. 14b Gratifyingly, in contrast to the one-methylene-tethered system, the reaction proceeded cleanly with no olefin migration observed.…”

Stereoselective Synthesis of Cyclopropanols

“…Some examples are illustrated in Table 3. Several examples [56][57][58][59] can be seen in Table 4. In the absence of any chelating substituents in the substrate, the products 140 are formed with high diastereoselectivity, i.e., the two substituents on the 1,2-disubstituted cyclopropanol preferentially end up in a cis relationship with one another.…”

New synthesis of syn-stereodiad building block for polyketides. Formal synthesis of arenamides A and C

“…Taking into account broad spectrum of biological activity of arenamides and keen interest of our research team in total and formal syntheses of natural compounds from hydroxy esters [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31], a novel procedure has been developed for the preparation of protected (3S,4S)-3-hydroxy-4-methyldecanoic acid 2 which is the most complex molecular fragment of macrolides 1a-1c (Scheme 1). The starting compound for the synthesis of 2 was (7S)-7-(3-bromoprop-1-en-2-yl)-5,5-dimethyl-4,6-dioxaspiro [2.5]octane (4).…”