197219-15-1Relevant articles and documents
Asymmetric synthesis of (-)-swainsonine, (+)-1,2-di-epi-swainsonine, and (+)-1,2,8-tri-epi-swainsonine
Lindsay, Karl B.,Pyne, Stephen G.
, p. 7774 - 7780 (2007/10/03)
The asymmetric synthesis of (-)-swainsonine via a nonchiral pool route that involves the Sharpless epoxidation to induce chirality is reported. The key steps involve vinyl epoxide aminolysis, ring-closing metathesis, and intramolecular N-alkylation to prepare the indolizidine ring and a highly diastereoselective cis-dihydroxylation using AD-mix-α. This synthetic strategy also allowed for the diastereoselective synthesis of (+)-1,2-di-epi-swainsonine and (+)-1,2,8-tri-epi-swainsonine.
The biomimetic construction of fused cyclic polyethers
Hayashi, Nobuyuki,Fujiwara, Kenshu,Murai, Akio
, p. 12425 - 12468 (2007/10/03)
The formation of fused cyclic ethers by biomimetic synthesis was demonstrated. The one-pot successive ring-expansion reactions of bromo diepoxides were investigated by regarding the epoxy groups as the nucleophiles for the intramolecular cationic carbons to obtain the fused cyclic ethers.