62158-33-2Relevant academic research and scientific papers
A Simple, Stereocontrolled Synthesis of a Thromboxane B2 Synthon
Kelly, Alan G.,Roberts, James S.
, p. 228 - 229 (1980)
A short stereocontrolled synthesis of a key intermediate in thromboxane B2 synthesis has been accomplished starting from the carbohydrate laevoglucosan.
A Short Synthesis of a Thromboxane B2 Key Intermediate from (R)-2,3-Isopropylideneglyceraldehyde. γ-Lactones as Templates for Chemoselective cis-Annulation of Pyranosides
Mulzer, Johann,Graske, Klaus-Dieter,Shanyoor, Mazin
, p. 593 - 598 (2007/10/02)
A six-step synthesis of the bicyclic lactone pyranoside 1, which has served as a key intermediate in numerous syntheses of thromboxane B2, from (R)-2,3-isopropylideneglyceraldehyde is described.In contrast to the previous syntheses of 1 the lactone part is prepared first and acts as a template in the annulation of the hemiketal unit.Further aspects of interest are the Felkin-Anh-controlled addition of vinyl cuprates to the acrylic ester 16 and the considerable rate difference in the formation of the γ-lactones 13, 14, 19, and 21 from the corresponding hydroxy acids. - Key Words: Thromboxane B2 key intermediate / Glyceraldehyde, (R)-isopropylidene / γ-Lactones / cis-Annulation / Felkin-Anh addition of vinyl cuprate
