Claims
- 1. A compound of structural formula I ##STR17## wherein one of R.sub.1 is alkenyl, alkynyl, aryl or cycloalkenyl, and the other is methyl, and where the bond at the C4-C5 position is a double bond it is trans, and wherein the bond at C2-C3 is cis or trans, and R.sub.2 is CH.sub.2 OH, CHO, COOH, or COO-alkyl, and wherein the cyclohexanone ring double bond may also be reduced.
- 2. A compound of structural formula Ia ##STR18## wherein, R.sub.1 is alkenyl, alkynyl, aryl or cycloalkenyl and where the bond at the C4-C5 position is a double bond it is trans, and wherein the bond at C2-C3 is cis or trans, and R.sub.2 is CH.sub.2 OH, CHO, COOH or COO-alkyl, and wherein the cyclohexanone ring double bond may also be reduced.
- 3. A compound according to claim 2, wherein structural formula Ia, R.sub.1 is selected from the group consisting of CH.sub.2 CH.dbd.CH.sub.2, CH.dbd.CH.sub.2, CCH and CH.sub.2 CCH.
- 4. A compound of structural formula Ib ##STR19## wherein, R.sub.1 is alkenyl, alkynyl, aryl or cycloalkenyl, and where the bond at the C4-C5 position is a double bond it is trans, and wherein the bond at C2-C3 is cis or trans, and R.sub.2 is CH.sub.2 OH, CHO, COOH, or COO-alkyl, and wherein the cyclohexanone ring double bond may also be reduced.
- 5. A compound according to claim 4, wherein structural formula Ib, R.sub.1 is selected from the group consisting of CH.sub.2 CH.dbd.CH.sub.2, CH.dbd.CH.sub.2, C.tbd.CH and CH.sub.2 CCH.
- 6. The compound according to claim 2, of structural formula ##STR20##
- 7. The compound according to claim 2, of structural formula
- 8. The compound according to claim 2, of structural formula
- 9. The compound according to claim 2 of structural formula
- 10. The compound according to claim 3, of structural formula
- 11. A method of making a compound of formula Ia, wherein, R.sub.1 is alkenyl, alkynyl, aryl, cycloalkenyl, other further substituted carbon chain including deuterium containing residues, and carbon containing substituents with heteroatoms and halogens; and when the bond at C4-C5 positions is a double bond it is trans and wherein the double bond at C2-C3 is cis or trans, and R.sub.2 is CH.sub.2 OH, CHO, COOH, COO-alkyl, or derivatives thereof, and wherein the cyclohexanone ring double bond may also be reduced, comprising
- (a) reacting 2,6-dimethylcylohexa-2,5-dien-1,4-dione or a derivative thereof, with the dianion of 3-methylpent-2-en-4-yn-1-ol or a hydroxyl protected derivative thereof, in the presence of a Grignard reagent of formula R.sub.1 MgX wherein X is Cl, Br or I, to effect conjugate addition of the unsaturated group, and where required
- (b) reduction of the C4-C5 triple bond to the trans double bond, and oxidation of the Cl hydroxyl to form functional derivatives thereof, and
- (c) when non-chiral starting material is employed, separating the (+) and (-) isomers by HPLC, and
- (d) further modification of the 8'-position by selective ozonolysis, and subsequent Wittig-type reactions onto the formed alehyde of 8'-methylene ABA.
- 12. A method of making a compound of formula Ib, ##STR21## wherein, R.sub.1 is alkenyl, alkynyl, aryl, cycloalkenyl, other further substituted carbon chain including deuterium containing residues, and carbon containing substituents with heteroatoms and halogens; and when the bond at C4-C5 positions is a double bond it is trans and wherein the double bond at C2-C3 is cis or trans, and R.sub.2 is CH.sub.2 OH, CHO, COOH, COO-alkyl, or derivatives thereof, and wherein the cyclohexanone ring double bond may also be reduced, comprising reacting
- (a) 2,6-dimethyl-4,4-ethylenedioxycyclohex-2-enone with R.sub.1 -I,
- (b) reacting the product so formed with the dianion of 3-methyl-pent-2-en-4-yn-1-ol, and where required
- (c) reduction of the C4-C5 triple bond to a double bond, and oxidation of the Cl alcohol to form functional derivatives thereof, and
- (d) separating the 8'-and 9'-R.sub.1 esters by HPLC.
- 13. A method according to claim 11 or 12, wherein step (a) the dione is used as starting material.
- 14. A method according to claim 11 or 12, wherein step (a) the C4-ketal of the dione is used as starting material.
- 15. A method according to claim 11, wherein step (a) a catalyst is included.
- 16. A method according to claim 15, wherein the catalyst is copper iodide.
- 17. A method according to any one of claims 11, 12, 15 or 16, wherein R.sub.1 is selected from the group consisting of CH.sub.2 CH.dbd.CH.sub.2, CH.dbd.CH.sub.2, C.tbd.CH, and CH.sub.2 CCH.
- 18. A method of affecting physiological processes in plants, known to be affected by natural ABA, comprising applying to the plant an effective amount of a compound as defined in any one of claims 1 to 10.
- 19. A method for the control of plant seed germination, comprising applying to the plant an effective amount of a compound as defined in any one of claims 1 to 10.
- 20. A method of enhancing antitranspirant activity in plants, comprising applying to the plant an effective amount of a compound as defined in any one of claims 1 to 10.
- 21. A method of enhancing ABA-inducible gene expression in plants, comprising applying to the plant an effective amount of a compound as defined in any one of claims 1 to 10.
- 22. A method of reducing transplantation shock in plant seedlings, comprising applying to the plant an effective amount of compounds as defined in any one of claims 1 to 10.
- 23. The method according to claim 22, wherein the plant is a spruce seedling, and the compound is applied as a root spray in a concentration of 10.sup.-3 to 10.sup.-4 M in an organic solvent.
Parent Case Info
This is the U.S. National Stage Application of PCT/CA96/00854 filed Dec. 20, 1996.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
102e Date |
371c Date |
PCT/CA96/00854 |
12/20/1996 |
|
|
9/22/1998 |
9/22/1998 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO97/23441 |
7/3/1997 |
|
|
US Referenced Citations (3)
Number |
Name |
Date |
Kind |
4209530 |
Visscher |
Jun 1980 |
|
5201931 |
Abrams et al. |
Apr 1993 |
|
5518995 |
Abrams et al. |
May 1996 |
|