FR2237901A1 - Vincamone and 21-epi-n-vincamone synthesis - from tabersone - Google Patents

Vincamone and 21-epi-n-vincamone synthesis - from tabersone

Info

Publication number
FR2237901A1
FR2237901A1 FR7424507A FR7424507A FR2237901A1 FR 2237901 A1 FR2237901 A1 FR 2237901A1 FR 7424507 A FR7424507 A FR 7424507A FR 7424507 A FR7424507 A FR 7424507A FR 2237901 A1 FR2237901 A1 FR 2237901A1
Authority
FR
France
Prior art keywords
vincamone
give
aspidospermidine
beta
alpha
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.)
Granted
Application number
FR7424507A
Other languages
French (fr)
Other versions
FR2237901B3 (en
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.)
Omnium Chimique SA
Original Assignee
Omnium Chimique 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 Omnium Chimique SA filed Critical Omnium Chimique SA
Publication of FR2237901A1 publication Critical patent/FR2237901A1/en
Application granted granted Critical
Publication of FR2237901B3 publication Critical patent/FR2237901B3/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D461/00—Heterocyclic compounds containing indolo [3,2,1-d,e] pyrido [3,2,1,j] [1,5]-naphthyridine ring systems, e.g. vincamine

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Title cpds are produced by a hemisynthesis starting from tabersone which is hydrogenated catalytically to give (-)-vincadiformine or 14,15-dihydrotabersonine, which on treatment with 2-moles of a peroxide give (-)-1,2-dehydro-16-carbomethyoxy-16-h ydroxy-N-oxy-aspidospermidine (I), followed by conversion of this cpd. to 16-oximino-aspidospermidine, which is an inter. for vincamine. (I) is saponified and decarboxylated to give 16-oxo-N-oxy-aspidospermidi ne, which is reduced to 16-oxo-aspidospermidine, which is coinverted to the corresp. oximino cpd. which is subjected to a Beckmann rearrangement to give a mixt. of 1 alpha-ethyl-1 beta-cyanoethyl-12 beta alpha-H (and beta-H) indolo [2,3 alpha] quinolizidine, which is sepd. by chromatography. These two cpds. when subjected to alkaline hydrolysis and cyclisation, give vincamone and 21-epi-vincamone resp.
FR7424507A 1973-07-16 1974-07-15 Vincamone and 21-epi-n-vincamone synthesis - from tabersone Granted FR2237901A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
BE133515A BE802387A (en) 1973-07-16 1973-07-16 PROCESS FOR PREPARING VINCAMONE AND EPI-21 VINCAMONE FROM TABERSONIN AND NEW INDOLIC DERIVATIVES.

Publications (2)

Publication Number Publication Date
FR2237901A1 true FR2237901A1 (en) 1975-02-14
FR2237901B3 FR2237901B3 (en) 1977-05-20

Family

ID=3842080

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7424507A Granted FR2237901A1 (en) 1973-07-16 1974-07-15 Vincamone and 21-epi-n-vincamone synthesis - from tabersone

Country Status (2)

Country Link
BE (1) BE802387A (en)
FR (1) FR2237901A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1979000319A1 (en) * 1977-11-25 1979-06-14 Buzas Andre New indolo(2,3-a)quinolizidines,preparation and therapeutic use thereof
EP0013315A2 (en) * 1978-11-20 1980-07-23 Sumitomo Chemical Company, Limited Eburnane derivatives, their synthesis and pharmaceutical compositions containing them

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU187139B (en) * 1982-06-30 1985-11-28 Richter Gedeon Vegyeszet Process for preparing new eburnan derivatives
CH664569A5 (en) * 1984-04-12 1988-03-15 Consiglio Nazionale Ricerche PROCEDURE FOR THE PREPARATION OF EBURNAMONINE BY ELECTROCHEMISTRY.

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1979000319A1 (en) * 1977-11-25 1979-06-14 Buzas Andre New indolo(2,3-a)quinolizidines,preparation and therapeutic use thereof
EP0013315A2 (en) * 1978-11-20 1980-07-23 Sumitomo Chemical Company, Limited Eburnane derivatives, their synthesis and pharmaceutical compositions containing them
EP0013315A3 (en) * 1978-11-20 1980-10-15 Sumitomo Chemical Company Limited Eburnane derivatives, including intermediates, their synthesis and pharmaceutical compositions containing them
EP0042526A1 (en) * 1978-11-20 1981-12-30 Sumitomo Chemical Company, Limited Process for producing apovincaminic acid esters and their salts

Also Published As

Publication number Publication date
BE802387A (en) 1973-11-16
FR2237901B3 (en) 1977-05-20

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