GB868478A - Synthesis of deserpidine - Google Patents
Synthesis of deserpidineInfo
- Publication number
- GB868478A GB868478A GB15679/58A GB1567958A GB868478A GB 868478 A GB868478 A GB 868478A GB 15679/58 A GB15679/58 A GB 15679/58A GB 1567958 A GB1567958 A GB 1567958A GB 868478 A GB868478 A GB 868478A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methoxy
- lactone
- carboxy
- hydroxy
- yohimbane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises the dextro-rotatory lactone of 18b -hydroxy-17a -methoxy-16b -carboxy-20a -D 3,14-yohimbene and the laevorotatory lactone of 18b -hydroxy-17a -methoxy-16b -carboxy-3a ,20a -yohimbane and a process for the synthesis of deserpidine (also rescinnamine) characterized in that laevorotatory 1b -carboxymethyl-2b -methoxycarbonyl-3a - methoxy-4b - acetoxy -6b - formylcyclohexane methyl ester is condensed with tryptamine, the resulting 18b -acetoxy-17a -methoxy- 16b - methoxycarbonyl- 2,3- 3, 4-diseco-D 4,21-dehydro-20a -yohimbane-3-oic acid methyl ester is reduced, cyclized and saponified to give dextrorotatory-18b -hydroxy-17a -methoxy-16b - carboxy-2, 3- seco-3- oxo- 20a -yohimbane, which is lactonised and the laevoratatory lactone cyclised to give the dextrorotatory lactone of 18b -hydroxy-17a -methoxy-16b - carboxy-20a - D 3, 14-yohimbene, which is reduced to dextrorotatory lactone of 18b - hydroxy- 17a - methoxy- 16b - carboxy-3b ,20a -yohimbane, which upon methanolysis to methyl deserpidate and then esterification with a functional derivative of trimethoxybenzoic or -cinnamic acid gives deserpidine or rescinnamine respectively. Detailed examples illustrate the above process. Specifications 809,912, 868,475 and 868,485 are referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR868478X | 1957-05-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB868478A true GB868478A (en) | 1961-05-17 |
Family
ID=9346153
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB15679/58A Expired GB868478A (en) | 1957-05-22 | 1958-05-15 | Synthesis of deserpidine |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB868478A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005095394A1 (en) * | 2004-03-25 | 2005-10-13 | Indena S.P.A. | A process for the semisynthesis of deserpidine |
-
1958
- 1958-05-15 GB GB15679/58A patent/GB868478A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005095394A1 (en) * | 2004-03-25 | 2005-10-13 | Indena S.P.A. | A process for the semisynthesis of deserpidine |
US7468438B2 (en) | 2004-03-25 | 2008-12-23 | Indena S.P.A. | Process for the semisynthesis of deserpidine |
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