Strigolactone formulations and uses thereof
Disclosed herein are plant propagation materials, methods of manufacturing, formulations and uses thereof. The plant propagation materials disclosed herein may comprise a strigolactone obtained by a biosynthetic process. The plant propagation material may comprise a chemical mimic of a strigolactone. The strigolactone may be 5-deoxystrigol. Methods of manufacturing the plant propagation materials may comprise a chemical process. Alternatively, methods of manufacturing the plant propagation material may comprise a biosynthetic process. The methods may comprise use of one or more polynucleotides. The polynucleotides may encode a metabolite. The polynucleotides may comprise one or more genes encoding one or more components of a strigolactone pathway.
1. A method of making a compound of Formula (I), comprising:
a) contacting sclareolide with methyl formate to form a mixture; and
b) contacting said mixture with
wherein R 17 is H, alkyl, halo, or haloalkyl, and X is Cl, Br, or I,
wherein Formula (I) has the structure of:
wherein:
a is 1,b is 2, and c is 0;
each A is independently O;
each E is independently O;
each G is independently C;
R 1 , R 5 , R 6 , and R 13 are methyl; and
R 2 , R 3 , R 4 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 14 , R 15 and R 16 are H.
2. The method of claim 1 , wherein said sclareolide comprises
3. The method of claim 1 , wherein said methyl formate is at least two fold excess of said sclareolide.
4. The method of claim 1 , further comprising dissolving said sclareolide in a tetrahydrofuran (THF) solution.
5. The method of claim 1 , further comprising contacting said sclareolide with a base solution.
6. The method of claim 5 , wherein said base solution comprises lithium diisopropylamide (LDA).
7. The method of claim 5 , wherein said base solution comprises potassium tert-butoxide.
8. The method of claim 1 , further comprising dissolving the mixture in a dimethylformamide (DMF) solution.
9. The method of claim 1 , further comprising contacting the mixture with potassium carbonate.
10. The method of claim 1 , wherein R 17 is alkyl.
11. The method of claim 1 , wherein R 17 is methyl.
12. The method of claim 1 , wherein X is Cl.
13. The method of claim 1 , wherein X is Br.
14. A method of making a compound of Formula (II), comprising:
a) contacting sclareolide with a base solution comprising lithium diisopropylamide (LDA) or potassium tert-butoxide;
b) contacting said sclareolide with methyl formate to form a mixture; and
c) contacting said mixture with
wherein Formula (II) has the structure of:
wherein:
a is 1, b is 2, and c is 0;
each A is independently O;
each E is independently O;
each G is independently C;
R 1 , R 5 , R 6 , R 13 , and R 17 are methyl; and
R 2 , R 3 , R 4 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 14 , R 15 and R 16 are H.