SU570255A1 - 6-ethoxyfulvene as key substance in a simplified scheme of complete synthesis of prostaglandiones or their analogs and method of its preparing - Google Patents
6-ethoxyfulvene as key substance in a simplified scheme of complete synthesis of prostaglandiones or their analogs and method of its preparingInfo
- Publication number
- SU570255A1 SU570255A1 SU762314722A SU2314722A SU570255A1 SU 570255 A1 SU570255 A1 SU 570255A1 SU 762314722 A SU762314722 A SU 762314722A SU 2314722 A SU2314722 A SU 2314722A SU 570255 A1 SU570255 A1 SU 570255A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- ethoxyfulvene
- analogs
- prostaglandiones
- preparing
- complete synthesis
- Prior art date
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Изобретение относитс к области полно ГО синтеза простагландинов или их аналогов , в частности к синтезу 6-этоксифульвена , вл ющегос новым ключевым веществом в названном синтезе. Известен способ полного синтеза про- стагландинов, основанный на использовании в качестве исходного вещества 5-метоксиметилциклопентадиена . Данна схема имеет следующие недостатки: нестабильность 5-метоксиметил- циклопентадиена, обусловленна подвижностью двойных св зей в циклопентадиеновом дре, что вызывает необходимость проведени синтеза и последующих превра шений вешества при низкой (до -2О°С)тем пературе, необходимость относительно сло ного к пгххход шего с небольшим выходом превршаени метоксиметильной группировки в промежуточных фрагментах в альдегидную группу. Использование в данной схеме 6-эток сифупьвона позвол ет исключить стадии преврац:еии и существенно упростить схе му синтеза. Кроме того, 6-этоксифульвен относительно стабилен и позвол ет значительно расширить температурные пределы реакции диеновой конденсаиии. Использование 6-алкоксифульвенов в данной схеме ранее не описано. Известен способ синтеза 6-метоксифульвена путем конденсации циклопентадиенилнатри с этиловьгм эфиром муравьиной кислоты с образованием натриевого производногю пиклопентадиенилальдегида (выход продукта 93%), алкилирование которого диметилсульфатом с выходом 55% дает 6-метрксифульвен . Обший выход составл ет около 50%. Недостатками известного способа вл ютс двухстадийность процесса, необходимость работы с токсичным диметилсульфатом , а также нестабильность 6- летоксифульвена , который самопроизвольно взрываетс при комнатной температуре. Цель изобретени - упрощение cxeNtbr ПОЛНОГО синтеза простагландинов или их аналогов и разрп(5отка способа получени The invention relates to the field of complete GO synthesis of prostaglandins or their analogues, in particular, to the synthesis of 6-ethoxyfulvena, which is a new key substance in this synthesis. A known method for the complete synthesis of prostaglandins, based on the use of 5-methoxymethylcyclopentadiene as the starting material. This scheme has the following disadvantages: instability of 5-methoxymethyl-cyclopentadiene, due to the mobility of double bonds in the cyclopentadiene core, which necessitates synthesis and subsequent transformations of the temperature at a low temperature (up to -2 ° C) with a small yield of conversion of the methoxymethyl group in the intermediate fragments into an aldehyde group. The use of the 6-etoc of sifupivon in this scheme makes it possible to exclude the stages of transformation: it significantly simplifies the synthesis scheme. In addition, 6-ethoxyfulvene is relatively stable and allows to significantly expand the temperature limits of the reaction of diene condensation. The use of 6-alkoxyfulvenes in this scheme is not previously described. A known method for the synthesis of 6-methoxy-fulvene by condensation of cyclopentadienyl sodium with ethyl ester of formic acid with the formation of sodium derivative of piclopentadienyl aldehyde (product yield 93%), the alkylation of which with dimethyl sulfate with a yield of 55% gives 6-meter-xyxyfluven. The overall yield is about 50%. The disadvantages of this method are the two-step process, the need to work with toxic dimethyl sulfate, as well as the instability of 6-letoxy fulvene, which spontaneously explodes at room temperature. The purpose of the invention is to simplify the cxeNtbr of the FULL synthesis of prostaglandins or their analogs and Razp (5
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU762314722A SU570255A1 (en) | 1976-01-19 | 1976-01-19 | 6-ethoxyfulvene as key substance in a simplified scheme of complete synthesis of prostaglandiones or their analogs and method of its preparing |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU762314722A SU570255A1 (en) | 1976-01-19 | 1976-01-19 | 6-ethoxyfulvene as key substance in a simplified scheme of complete synthesis of prostaglandiones or their analogs and method of its preparing |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU570255A1 true SU570255A1 (en) | 1979-10-15 |
Family
ID=20645766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762314722A SU570255A1 (en) | 1976-01-19 | 1976-01-19 | 6-ethoxyfulvene as key substance in a simplified scheme of complete synthesis of prostaglandiones or their analogs and method of its preparing |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU570255A1 (en) |
-
1976
- 1976-01-19 SU SU762314722A patent/SU570255A1/en active
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