Asymmetric synthesis of Pachastrissamine (Jaspine B) and its diastereomers viaη3-allylpalladium intermediates

Garner’s aldehyde as a versatile intermediate in the synthesis of enantiopure natural products

“…We have also successfully used ( Z )-vinyl nucleophiles created from the vinyl iodide 61 in the stereoselective synthesis of pachastrissamine ( 11 ) [81–82] and norfuranomycin [37] (Scheme 23). After halogen–metal exchange with n -BuLi, the newly formed nucleophile reacts with ( S ) -1 .…”

Aminohydroxylation of divinylcarbinol and its application to the synthesis of bicyclic hydroxypyrrolidine and aminotetrahydrofuran building blocks

“…In anti-cancer assays, this novel sphingosine derivative proved to be the most potent compound against the A549 human lung carcinoma cell line isolated from the Jaspis genus. The combination of potent biological properties and relatively straightforward molecular structures has led to the development of a number of its synthetic preparations (Llaveria et al, 2011;Passiniemi & Koskinen, 2011;Yoshimitsu et al, 2011;Srinivas Rao & Venkateswara Rao, 2011;Urano et al, 2010;Salma et al, 2010;Inuki et al, 2009Inuki et al, , 2010Yoshimitsu et al, 2010;Vichare & Chattopadhyay, 2010;Canals et al, 2009;Enders et al, 2008;Abraham et al, 2008, and the articles cited in their review). The biological activities of numerous synthetic analogues and epimers have also been prepared and tested.…”

Diastereoselective synthesis of vicinal amino alcohols

“…The products were then advanced to jaspine B and 3 of its diastereomers. 28,29 We were not happy with the performance of lithium acetylides or vinyl lithium species under anti-addition conditions. In search of a complementary method we turned to zinc nucleophiles which had been reported to add to α-chiral aldehydes in high anti-Felkin selectivity.…”