1440947-82-9Relevant academic research and scientific papers
Synthesis of (-)-morphine: Application of sequential claisen/claisen rearrangement of an allylic vicinal diol
Ichiki, Masato,Tanimoto, Hiroki,Miwa, Shohei,Saito, Ryosuke,Sato, Takaaki,Chida, Noritaka
, p. 264 - 269 (2013/02/25)
A detailed exploration of the synthesis of (-)-morphine based on sequential [3,3]-sigmatropic rearrangements is described. The sequential Claisen/Claisen rearrangements of an allylic vicinal diol resulted in the stereoselective formation of the two contiguous carbon centers, including a sterically encumbered quaternary carbon, in a single operation. The two ethyl esters generated in this reaction were successfully differentiated during a subsequent Friedel-Crafts-type cyclization. The (-)-morphine double bond was introduced at a late stage in our first-generation synthesis, but was formed at an earlier stage in the second-generation synthesis, resulting in a more efficient route to the end product.
