Title |
Synthesis of (−)‐Morphine: Application of Sequential Claisen/Claisen Rearrangement of an Allylic Vicinal Diol
|
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Published in |
Chemistry - A European Journal, November 2012
|
DOI | 10.1002/chem.201203284 |
Pubmed ID | |
Authors |
Masato Ichiki, Hiroki Tanimoto, Shohei Miwa, Ryosuke Saito, Takaaki Sato, Noritaka Chida |
Abstract |
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. |
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