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CasNo: 67309-95-9
MF: C15H22O4
Description |
Aspterric acid is a carotene-type sesquiterpene, plant growth regulator, and inhibitor of pollen development originally isolated from the fungus A. terreus. It inhibits pollen development, reduces stem length at first flowering, and increases the time to bolting and first flowering in A. thaliana when used at a concentration of 38 μM. Aspterric acid exerts its effects on reproductive growth in A. thaliana without inhibiting biosynthesis and transport of the plant growth regulator indole-3-acetic acid . |
Uses |
Aspterric acid is an antibiotic compound. |
General Description |
Natural product derived from fungal source. |
InChI:InChI=1/C15H22O4/c1-9(2)10-5-6-15-7-13(18-8-15)11(14(16)19-17)3-4-12(10)15/h11-13,17H,3-8H2,1-2H3/t11-,12+,13-,15?/m1/s1
Total synthesis of dl-aspterric acid (1)...
A carotane type sesquiterpene, aspterric...
(1S,5S,8R,9R)-8-Acetoxy-4-isopropylidene-10-oxa-tricyclo[7.2.1.01,5]dodecane-8-carboxylic acid methyl ester
dl-aspterric acid
Conditions | Yield |
---|---|
With sodium hydroxide; In methanol; 1.) room temp.; 2.) 50 deg C, 18 h;;
|
76% |
(1R,5R,8R,9S)-8-Acetoxy-4-isopropylidene-10-oxa-tricyclo[7.2.1.01,5]dodecane-8-carboxylic acid methyl ester
(1R,5R,8R,9S)-8-Hydroxy-4-isopropylidene-10-oxa-tricyclo[7.2.1.01,5]dodecane-8-carboxylic acid
Conditions | Yield |
---|---|
With sodium hydroxide; In methanol; Ambient temperature;
|
61% |
(1R,4R,6S,9R,10S)-9-Acetoxy-4-hydroxy-5,5-dimethyl-11-oxa-tricyclo[8.2.1.01,6]tridecane-9-carboxylic acid methyl ester
(1R,5R,8R,9S)-8-Acetoxy-4-isopropylidene-10-oxa-tricyclo[7.2.1.01,5]dodecane-8-carboxylic acid methyl ester
(1R,4R,6S,9S,10S)-9-Methoxy-5,5-dimethyl-4-trimethylsilanyloxy-11-oxa-tricyclo[8.2.1.01,6]tridecane-9-carbonitrile
(1R,4R,6S,9R,10S)-4,9-Dihydroxy-5,5-dimethyl-11-oxa-tricyclo[8.2.1.01,6]tridecane-9-carboxylic acid methyl ester