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Total synthesis of thaxtomin A analogues and their intermediates
US8993762B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-8993762-B2 |
| Application number | US-201313840975-A |
| Country | US |
| Kind code | B2 |
| Filing date | Mar 15, 2013 |
| Priority date | Mar 15, 2013 |
| Publication date | Mar 31, 2015 |
| Grant date | Mar 31, 2015 |
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Abstract
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Improved synthetic methods for the production of thaxtomin analogs, particularly thaxtomin A, and intermediates therefore such as substituted tryptophans and in particular, 4-nitro-L-tryptophan, and substituted phenyl acrylic acids are disclosed. Bioassays show that the synthetic thaxtomin A is not significantly different from the natural one in herbicidal activity.
First claim
Opening claim text (preview).
What is claimed is: 1. A method for the synthesis of a thaxtomin or analog thereof having the structure (I) wherein R1 is NO 2 and R2 is selected from a lower alkyl, hydroxyl, halogen, fluoromethyl, difluoromethyl, trifluoromethyl, nitro, amine, methoxy, fluoromethoxy, difluoromethoxy, and trifloromethoxy, comprising: (a) reacting a tryptophan amide analog having the structure with substituted phenyl acrylic acid having the structure wherein R is selected from a lower alkyl, hydroxyl, halogen, fluoromethyl, difluoromethyl, trifluoromethyl, nitro, amine, methoxy, fluoromethoxy, difluoromethoxy, and trifloromethoxy, or its keto tautomer to obtain a compound having the structure (A2) wherein R1 is NO 2 and R2 is selected from a lower alkyl, hydroxyl, halogen, fluoromethyl, difluoromethyl, trifluoromethyl, nitro, amine, methoxy, fluoromethoxy, difluoromethoxy, and trifloromethoxy; and (b) subjecting the compound having the structure (A2) to a cyclization agent to obtain the structure (I). 2. The method according to claim 1 , wherein said thaxtomin analogue is thaxtomin A having the structure 3. The method according to claim 1 , wherein said substituted phenylacrylic acid has the structure wherein R is OH or its keto tautomer. 4. The method according to claim 3 , wherein said substituted phenylacrylic acid has the structure 5. The method according to claim 1 , wherein the cyclization is by means of an organic base. 6. The method according to claim 5 wherein the organic base is potassium hydroxide. 7. The method according to claim 5 , wherein the organic base is a chiral Lewis base. 8. The method according to claim 5 wherein the organic base is selected from the group consisting of substituted or unsubstituted pyridine, amine, imidazole, benzimidazole, histidine, and phosphazene.
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- C07D403/06Primary
linked by a carbon chain containing only aliphatic carbon atoms · CPC title
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- What does patent US8993762B2 cover?
- Improved synthetic methods for the production of thaxtomin analogs, particularly thaxtomin A, and intermediates therefore such as substituted tryptophans and in particular, 4-nitro-L-tryptophan, and substituted phenyl acrylic acids are disclosed. Bioassays show that the synthetic thaxtomin A is not significantly different from the natural one in herbicidal activity.
- Who is the assignee on this patent?
- Marrone Bio Innovations Inc, Marrone Bio Innovations Inc
- What technology area does this patent fall under?
- Primary CPC classification C07D403/06. Mapped technology areas include Chemistry & Metallurgy.
- When was this patent published?
- Publication date Tue Mar 31 2015 00:00:00 GMT+0000 (Coordinated Universal Time) (B2). Legal status and post-grant events are not shown on this page.
- What related patents are in patentsdb?
- We list 8 related publications on this page (citations in our corpus or others sharing the same primary CPC).