3′-substituted-abscisic acid derivatives

Patent metadata

Field	Value
Publication number	US-9781930-B2
Application number	US-201514794415-A
Country	US
Kind code	B2
Filing date	Jul 8, 2015
Priority date	Jul 8, 2014
Publication date	Oct 10, 2017
Grant date	Oct 10, 2017

Abstract

The invention relates to a novel class of (S)-3′-substituted-abscisic acid derivatives and (±)-3′-substituted-abscisic acid derivatives, and methods of synthesizing the derivatives.

First claim

What is claimed is:

1. An enantiomerically pure compound of Formula I:

wherein:
n is 1;
R 1 is naphthyl or substituted naphthyl or heteroaryl;
R 2 is hydrogen;
and salts thereof.

2. A process of making the compounds of claim 1 comprising:
a. reacting (S)-abscisic acid with an alkylating agent to form an ester;
b. treating the compound resulting from Step a with a base and an alkylating agent in a solvent; and
c. hydrolyzing the compound resulting from Step b.

3. A method of regulating plant growth comprising applying an effective amount of at least one of the compounds of claim 1 to a plant in need of growth regulation.

4. A process of making the compounds of claim 1 comprising:
a. regioselective alkylation of 2,6,6-trimethylcyclohex-2-ene-1,4-dione to give 3-substituted-2,6,6-trimethylcyclohex-2-ene-1,4-dione (Structure B below);

b. conversion of compounds of Structure B to 3-substituted-1-((1E,3Z)-5-hydroxy-3-methylpenta-1,3-dien-1-yl)-2,6,6-trimethylcyclohex-2-ene-1,4-diol (Structure F below);

c. oxidation of compounds of Structure F to (2Z,4E)-5-(3-substituted-1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)-3-methylpenta-2,4-dienal (Structure G below); and

d. oxidation of compounds of Structure G.

Assignees

• Valent Biosciences Corp
• Valent Biosciences Llc

Inventors

• Wang Gary T
• Heiman Daniel
• Venburg Gregory D
• Nagano Eiki
• Surpin Marci
• Lustig Joseph H

Classifications

• C07C235/78

  the carbon skeleton containing rings · CPC title

• C07C253/30

  by reactions not involving the formation of cyano groups · CPC title

• C07C2601/16

  the ring being unsaturated · CPC title

• C07C67/44

  by oxidation-reduction of aldehydes, e.g. Tishchenko reaction · CPC title

• C07C69/738

  Esters of keto-carboxylic acids {or aldehydo-carboxylic acids} · CPC title