GB868478A - Synthesis of deserpidine - Google Patents

Synthesis of deserpidine

Info

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
Application number
GB15679/58A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Laboratoires Francais de Chimiotherapie SA
Original Assignee
Laboratoires Francais de Chimiotherapie SA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Laboratoires Francais de Chimiotherapie SA filed Critical Laboratoires Francais de Chimiotherapie SA
Publication of GB868478A publication Critical patent/GB868478A/en
Expired legal-status Critical Current

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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.
GB15679/58A 1957-05-22 1958-05-15 Synthesis of deserpidine Expired GB868478A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (2)

* Cited by examiner, † Cited by third party
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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