Total Synthesis Of Stagonolide Research Articles

ChemInform Abstract: Asymmetric Total Synthesis of Stagonolide F.

Abstract A highly convergent stereoselective total synthesis of stagonolide F is described starting from commercially available 5-hexen 1-ol using asymmetric dihydroxylation, Jacobsen's hydrolytic kinetic resolution (HKR), regioselective epoxide ring opening with vinyl Grignard reaction, esterification, and ring-closing metathesis (RCM) as key steps.

Asymmetric Total Synthesis of Stagonolide F

A highly convergent stereoselective total synthesis of stagonolide F is described starting from commercially available 5-hexen 1-ol using asymmetric dihydroxylation, Jacobsen's hydrolytic kinetic resolution (HKR), regioselective epoxide ring opening with vinyl Grignard reaction, esterification, and ring-closing metathesis (RCM) as key steps.

Total synthesis of stagonolide B

Asymmetric total synthesis of nonenolide stagonolide-B has been presented in this Letter. The main highlight of our synthetic strategy is the application of hydroxynitrile lyase (ParsHNL) mediated asymmetric synthesis of cyanohydrin, Sharpless asymmetric dihydroxylation, cross metathesis (CM) reaction, stereoselective Keck allylation reaction and Yamaguchi macrolactonization at a late stage enables us to achieve the synthesis of the target molecule in an efficient way.

Synthesis of stagonolide C from Mulzer epoxide

Total synthesis of stagonolide C using chiral pool strategy is described. The two key intermediates were prepared from l-glutamic acid and d-glucono-1,5-lactone, followed by Julia–Lythgoe olefination and Yamaguchi esterification to afford the target compound in an efficient way.

Effect of the allylic substituents on ring closing metathesis: the total synthesis of stagonolide B and 4-epi-stagonolide B

The total syntheses of stagonolide B and its 4-epimer were carried out to probe into how the relative stereochemistry of allylic hydroxy groups and their protecting groups influence the efficiency of the ring closing metathesis.