PROCESS FOR THE PRODUCTION OF SPRINGENE

Abstract

The application relates to a process for the production of alpha-springene (formula (I)) and beta-springene (formula (II)) from geranyl geranyl acetate (formula (III)).

##STR00001##

Claims

1. Process to produce a mixture of a compound of formula (I) ##STR00005## and a compound of formula (II) ##STR00006## wherein a compound of formula (III) ##STR00007## is heated in the presence of a catalyst.

2. Process according to claim 1, wherein the reaction is carried out in at least one polar aprotic solvent (preferably DMSO).

3. Process according to claim 1, wherein the reaction of step (i) is carried out at a temperature of 30 C. 120 C.

4. Process according to claim 1, wherein the reaction of step (i) is carried out under an inert gas atmosphere.

5. Process according to claim 1, wherein catalyst is chosen from a strong base chosen from the group consisting of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), Trger base ((1RS,9RS)-5,13-dimethyl-1,9-diazatetracyclo [7.7.1.02,7.010,15]hepta-deca-2(7),3,5,10(15),11,13-hexaene), polyaminophosphazenes (Schwesinger superbases), and 1,4-diazabicyclo[2.2.2]octane (DABCO) and a transition metal complex chosen from the group consisting of Ni(PPh.sub.3).sub.4, Pd(PPh.sub.3).sub.4, Pt(PPh.sub.3).sub.4, Ni(PoTol.sub.3).sub.4, Pd(PoTol.sub.3).sub.4, Pt(PoTol.sub.3).sub.4, Ni(OPPh.sub.3).sub.4, Pd(OPPh.sub.3).sub.4, Pt(OPPh.sub.3).sub.4, Ni(P(C.sub.1-6-alkyl).sub.3).sub.4, Pd(P(C.sub.1-6-alkyl).sub.3).sub.4 and Pt(P(C.sub.1-6-alkyl).sub.3).sub.4, wherein the C.sub.1-6-alkyl can be linear or branched.

Description

EXAMPLES

Example

Example 1: Elimination of acetic acid from geranylgeranyl acetate

[0026] Under inert gas atmosphere, geranylgeranyl acetate (1.3 mmol) was dissolved in anhydrous DMSO (2.5 ml). With stirring DBU (2 eq.) and Pd(PPh.sub.3).sub.4 (7 mol %) were added and the reaction mixture was warmed to 60 C. within 15 min. After 3 hours reaction time, the mixture was cooled to room temperature and transferred into a separation funnel with 20 ml of ethyl acetate. The organic phase was washed with water (220 ml) and brine (20 ml). The aqueous layers were extracted with ethyl acetate (320 ml). The combined organic layers were dried over MgSO.sub.4 and concentrated under reduced pressure. The product was obtained as an isomeric mixture of - and -springene (7:3) in 66% yield.