328381-98-2Relevant academic research and scientific papers
Synthesis of sialic acid derivatives based on chiral substrate-controlled stereoselective aldol reactions using pyruvic acid oxabicyclo[2.2.2]octyl orthoester
Norimura, Yusuke,Yamamoto, Daisuke,Makino, Kazuishi
supporting information, p. 640 - 648 (2017/01/25)
The synthesis of sialic acids and their analogs was accomplished based on substrate-controlled asymmetric aldol reactions between sterically complicated aldehydes easily prepared from commercially available carbohydrates and a novel pyruvic acid oxabicyclo[2.2.2]octyl orthoester. Systematic aldol reaction studies using chiral aldehydes revealed that α,β,γ-benzyloxy-substituted aldehydes with an α,β-anti relative configuration preferentially provided the Felkin products with the 4,5-anti configuration with high diastereoselectivity. The relative β,γ-configuration in α,β,γ-benzyloxy-substituted aldehydes with an α,β-syn arrangement exerted a secondary effect on the diastereoselectivity of the stereogenic center formed in aldol reactions, and α,β-syn-β,γ-anti benzyloxyaldehyde exhibited superior diastereoselectivity to α,β-syn-β,γ-syn benzyloxyaldehyde to yield the Felkin products.
Total synthesis of lankacyclinol
Williams, David R.,Cortez, Guillermo S.,Bogen, Stephane L.,Rojas, Christian M.
, p. 4612 - 4615 (2007/10/03)
An antitumor agent from various Streptomyces species, the title compound 1, has been synthesized for the first time, as described here. Key steps involved include a ring-closing metathesis, a photochemically induced acylnitrene insertion process, and high
