68877-57-6Relevant articles and documents
Asymmetric addition of alkoxy ethynyl anion to chiral N-sulfinyl imines
Verrier, Charlie,Carret, Sebastien,Poisson, Jean-Francois
, p. 5122 - 5125 (2012)
The addition of lithiated ynol ethers to chiral N-sulfinyl imines proceeds in high yield and diastereoselectivity. The selectivity is completely reversed by the addition of boron trifluoride. These alkoxypropargyl sulfinamides can be reduced to afford eno
Total synthesis of the anticancer natural product OSW-1
Yu, Wensheng,Jin, Zhendong
, p. 6576 - 6583 (2007/10/03)
The highly potent anticancer natural saponin OSW-1 has been successfully synthesized from commercially available 5-androsten-3β-ol-17-one 79 in 10 operations with 28% overall yield. The key steps in the total synthesis included a highly regio- and stereoselective selenium dioxide-mediated allylic oxidation of 80 and a highly stereoselective 1,4-addition of α-alkoxy vinyl cuprates 68 to steroid 17(20)-en-16-one 12E to introduce the steroid side chain. This total synthesis demonstrated once again the versatile synthetic applications of α-halo vinyl ether chemistry developed in our laboratories.
The photochemistry of acetylenic ethers. A novel carbon-oxygen to carbon-carbon bond conversion
Smith, Bradley A.,Callinan, Andrew J.,Swenton, John S.
, p. 2283 - 2286 (2007/10/02)
Irradiation of acetylenic ethers in methanol gives homologated esters via a formal [1,3]-oxygen-to-carbon migration involving a ketene intermediate.