DD229127A1 - PROCESS FOR PREPARING 16,17-DICHLOR GIBBERELLINES - Google Patents
PROCESS FOR PREPARING 16,17-DICHLOR GIBBERELLINES Download PDFInfo
- Publication number
- DD229127A1 DD229127A1 DD26970184A DD26970184A DD229127A1 DD 229127 A1 DD229127 A1 DD 229127A1 DD 26970184 A DD26970184 A DD 26970184A DD 26970184 A DD26970184 A DD 26970184A DD 229127 A1 DD229127 A1 DD 229127A1
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- gibberellin
- gibberellins
- ent
- gibberellan
- acetone
- Prior art date
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Es ist das Ziel der Erfindung, solche Gibberellin-Derivate herzustellen, die eine veraenderte biologische Aktivitaet aufweisen. Die Aufgabe der Erfindung besteht darin, in die Positionen 16 und 17 des ent-Gibberellan-Grundgeruests stereospezifisch Chloratome einzufuehren. Erfindungsgemaess wird ein Gibberellin-Derivat mit einer 16,17-Methylen-Gruppierung in einem organischen Loesungsmittel mit Phenyljoddichlorid unter Bestrahlung mit UV- oder sichtbarem Licht umgesetzt.It is the object of the invention to prepare such gibberellin derivatives which have altered biological activity. The object of the invention is to introduce into the positions 16 and 17 of the ent-gibberellan skeleton stereospecific chlorine atoms. According to the invention, a gibberellin derivative having a 16,17-methylene moiety in an organic solvent is reacted with phenyl iodine dichloride under irradiation with UV or visible light.
Description
Beispiel 2 leS^-Dichlor-diacetylgibberellin A3 (4)Example 2 leSi-dichloro-diacetylgibberellin A 3 (4)
Die Herstellung erfolgt analog Beispiel 1 aus Diacetylgibberellin A3 (2) in Chloroform (60% Ausbeute). 16S, 17-Dichlordiacetylgibberellin kristallisiert aus Chloroform/Hexan: Schmp. 205-2080C, [α]" +86.7° (c = 0,438, Chloroform). IR (Nujol): 1725(Carbonyl), 1750 (γ-Lacton),3200cm"1 (Carboxyl OH). MS: m/z499 (M-D,464(m-HCL). NMR (200 MHz,CDCI3): 1,19 (s, 18-H3), 206 (s, CH3COO), 2,12 (s, CH3COO), 2,81 (d, J = 10 Hz, 6-H), 3,27 (d, J = 10 Hz, 5-H), 4,07 und 4,22 (2xd, J = 13 Hz, 17-H2), 5,34 (d, J = 4 Hz, 3-H), 5,90 (dd, J = 4 Hz, J' = 10 Hz, 2-H), 6,37 (δ) ppm (d, J = 10 Hz, 1-H).The preparation is carried out analogously to Example 1 from diacetylgibberellin A 3 (2) in chloroform (60% yield). 16S, 17-Dichlordiacetylgibberellin crystallized from chloroform / hexane. M.p. 205-208 0 C, [α] "+ 86.7 ° (c = 0.438, chloroform) IR (Nujol):. 1725 (carbonyl), 1750 (γ-lactone) , 3200 cm -1 (carboxyl OH). MS: m / z499 (MD, 464 (m-HCL). NMR (200 MHz, CDCl 3 ): 1.19 (s, 18-H 3 ), 206 (s, CH 3 COO), 2.12 (s , CH 3 COO), 2.81 (d, J = 10Hz, 6-H), 3.27 (d, J = 10Hz, 5-H), 4.07 and 4.22 (2xd, J = 13 Hz, 17-H 2 ), 5.34 (d, J = 4 Hz, 3-H), 5.90 (dd, J = 4 Hz, J '= 10 Hz, 2-H), 6.37 (δ) ppm (d, J = 10 Hz, 1-H).
H COOH H COOH
H COOH H COOH
Cl "CH2ClCl "CH 2 Cl
1: R = H 2: R = Ac3:R s :R =.Ac1: R = H 2: R = Ac 3: R s: R = .Ac
Claims (4)
Beispiel 1
16S,17-Dichlor-gibberellin A3 (3)embodiments
example 1
16S, 17-dichloro-gibberellin A 3 (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DD26970184A DD229127A1 (en) | 1984-11-21 | 1984-11-21 | PROCESS FOR PREPARING 16,17-DICHLOR GIBBERELLINES |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DD26970184A DD229127A1 (en) | 1984-11-21 | 1984-11-21 | PROCESS FOR PREPARING 16,17-DICHLOR GIBBERELLINES |
Publications (1)
Publication Number | Publication Date |
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DD229127A1 true DD229127A1 (en) | 1985-10-30 |
Family
ID=5562425
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DD26970184A DD229127A1 (en) | 1984-11-21 | 1984-11-21 | PROCESS FOR PREPARING 16,17-DICHLOR GIBBERELLINES |
Country Status (1)
Country | Link |
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DD (1) | DD229127A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0599939A1 (en) * | 1991-08-15 | 1994-06-08 | Commonwealth Scientific And Industrial Research Organisation | Method of treating plants or plant tissues |
-
1984
- 1984-11-21 DD DD26970184A patent/DD229127A1/en not_active IP Right Cessation
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0599939A1 (en) * | 1991-08-15 | 1994-06-08 | Commonwealth Scientific And Industrial Research Organisation | Method of treating plants or plant tissues |
EP0599939A4 (en) * | 1991-08-15 | 1994-08-17 | Lloyd Thomas Evans | Method of treating plants or plant tissues. |
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