171032-82-9Relevant academic research and scientific papers
New Chiral Building Blocks from 1,2;5,6-Di-O-isopropylidene-D-mannitol: Synthesis of C2-Symmetrical and Unsymmetrical Mono- and Bisepoxides and of a Polyhydroxylated Butenolide
Mulzer, Johann,Pietschmann, Catarina,Schoellhorn, Bernd,Buschmann, Juergen,Luger, Peter
, p. 1433 - 1440 (2007/10/02)
The enantiopure epoxides 2-6 were synthesized from 1,2;5,6-di-O-isopropylidene-D-mannitol (1).The terminal epoxides 2 and 3 are available from the desoxy mannitol 9 in three steps.The C2-symmetrical epoxides 4 and 5 were generated via the C-4-inverted alcohol 15.The C2-symmetrical bisepoxide 6 was prepared in a short sequence maintaining the symmetry throughout the entire synthesis.The crystalline butenolide 44 was prepared in five steps from 1 by Wittig olefination and lactonization. - Key Words: Epoxides, C2-symmetrical / Bisepoxides / Butenolide, polyhydroxylated
