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| | Tropinone Basic information |
| | Tropinone Chemical Properties |
| | Tropinone Usage And Synthesis |
| Chemical Properties | Tropinone is a white to light yellow crystal powder, It is an alkaloid and a precursor to a number of additional plant alkaloids. Tropinone is the first intermediate in the biosynthesis of the pharmacologically important tropane alkaloids that possesses the 8-azabicyclo[3.2.1]octane core bicyclic structure that defines this alkaloid class. Chemical synthesis of tropinone was achieved in 1901 but the mechanism of tropinone biosynthesis has remained elusive. | | Uses | Tropinone is an oxidative product of Tropane, used to synthesize Morphine and Tropane alkaloids. | | Preparation | The first synthesis of tropinone was by Richard Willstätter in 1901. It started from the seemingly related cycloheptanone, but required many steps and had an overall yield of only 0.75%.Willstätter had previously synthesized cocaine from tropinone, in what was the first synthesis and elucidation of the structure of cocaine.
The 1917 synthesis by Robinson is considered a legend in total synthesis due to its simplicity and biomimetic approach. Tropinone is a bicyclic molecule, but the reactants used in its preparation are fairly simple: succinaldehyde, methyl amine and acetone dicarboxylic acid (or even acetone). The synthesis is a good example of a biomimetic reaction or biogenetic-type synthesis because biosynthesis makes use of the same building blocks. It also demonstrates a tandem reaction in a one-pot synthesis. Furthermore the yield of the synthesis was 17% and with subsequent improvements exceeded 90%. | | References | 1. Arthur J. Birch. Investigating a Scientific Legend: The Tropinone Synthesis of Sir Robert Robinson, F.R.S. Notes and Records of the Royal Society of London, 1993, 47, 277-296. DOI:10.1098/rsnr.1993.0034
2. Andrew J. Humphrey and David O'Hagan. Tropane alkaloid biosynthesis. A century old problem unresolved. Natural Products Reports 2001, 18, 494-502. DOI:10.1039/b001713m
3. Tropinone synthesis via an atypical polyketide synthase and P450-mediated cyclization DOI:10.1038/s41467-018-07671-3
4. R. Robinson (1917). "A synthesis of tropinone". Journal of the Chemical Society, Transaction 111: 762 - 768. doi:10.1039/CT9171100762 |
| | Tropinone Preparation Products And Raw materials |
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