67309-95-9

Basic information

• Product Name: Aspterric acid
• Synonyms: Aspterric acid;(3R,4R,6aS,9aS)-Octahydro-4-hydroxy-7-(1-methylethylidene)-1H-3,9a-methanocyclopent[c]oxocin-4-carboxylic acid
• CAS NO: 67309-95-9
• Molecular Formula: C15H22O4
• Molecular Weight: 266.33278
• Mol File: 67309-95-9.mol

Chemical Properties

• Boiling Point: 405.8°Cat760mmHg
• Flash Point: 148.4°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 2.83E-08mmHg at 25°C
• Refractive Index: 1.542
• Storage Temp.: ?20°C
• Solubility: Soluble in DMSO
• PKA: 3.42±0.20(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: Aspterric acid(CAS DataBase Reference)
• NIST Chemistry Reference: Aspterric acid(67309-95-9)
• EPA Substance Registry System: Aspterric acid(67309-95-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 67309-95-9(Hazardous Substances Data)

Usage

References

1) Tsuda et al. (1978), Aspterric acid, a new sesquiterpenoid of the carotene group, a metabolite from Aspergillus terreus IFO-6123. X-Ray crystal and molecular structure of its p-bromobenzoate; J. Chem. Soc. Chem. Commun., 4 161 2) Yan et al. (2018), Resistance-gene-directed discovery of a natural-product herbicide with a new mode of action; Nature., 559 415 3) Shimada et al. (2002), Aspterric acid and 6-hydroxymellein, inhibitors of pollen development in Arabidopsis thaliana, produced by Aspergillus terreus; Z. Naturforsch. C., 57 459

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

Upstream product

• 112609-29-7 (1R,4R,6S,9S,10S)-4,9-Diacetoxy-5,5-dimethyl-11-oxa-tricyclo[8.2.1.0^1,6]tridecane-9-carboxylic acid methyl ester 
• 112609-20-8 (1R,4R,6S,9S,10S)-4-Hydroxy-9-methoxy-5,5-dimethyl-11-oxa-tricyclo[8.2.1.0^1,6]tridecane-9-carboxylic acid methyl ester 
• 112609-28-6 (1R,4R,6S,9S,10S)-4,9-Dihydroxy-5,5-dimethyl-11-oxa-tricyclo[8.2.1.0^1,6]tridecane-9-carboxylic acid methyl ester 
• 89330-03-0 (1R,4R,6S,9R,10S)-9-Methoxy-5,5-dimethyl-4-trimethylsilanyloxy-11-oxa-tricyclo[8.2.1.0^1,6]tridecane-9-carbonitrile 
• 67309-99-3 (1S,5S,8R,9R)-8-Acetoxy-4-isopropylidene-10-oxa-tricyclo[7.2.1.0^1,5]dodecane-8-carboxylic acid methyl ester 
• 89330-04-1 (1R,4R,6S,9S,10S)-9-Acetoxy-4-hydroxy-5,5-dimethyl-11-oxa-tricyclo[8.2.1.0^1,6]tridecane-9-carboxylic acid methyl ester 
• 112609-29-7 (1R,4R,6S,9R,10S)-4,9-Diacetoxy-5,5-dimethyl-11-oxa-tricyclo[8.2.1.0^1,6]tridecane-9-carboxylic acid methyl ester 
• 112609-20-8 (1R,4R,6S,9R,10S)-4-Hydroxy-9-methoxy-5,5-dimethyl-11-oxa-tricyclo[8.2.1.0^1,6]tridecane-9-carboxylic acid methyl ester 
• 112609-28-6 (1R,4R,6S,9R,10S)-4,9-Dihydroxy-5,5-dimethyl-11-oxa-tricyclo[8.2.1.0^1,6]tridecane-9-carboxylic acid methyl ester 
• 89330-03-0 (1R,4R,6S,9S,10S)-9-Methoxy-5,5-dimethyl-4-trimethylsilanyloxy-11-oxa-tricyclo[8.2.1.0^1,6]tridecane-9-carbonitrile 
• 67309-99-3 (1R,5R,8R,9S)-8-Acetoxy-4-isopropylidene-10-oxa-tricyclo[7.2.1.0^1,5]dodecane-8-carboxylic acid methyl ester 
• 89330-04-1 (1R,4R,6S,9R,10S)-9-Acetoxy-4-hydroxy-5,5-dimethyl-11-oxa-tricyclo[8.2.1.0^1,6]tridecane-9-carboxylic acid methyl ester 

Relevant articles and documents

Synthetic Studies on dl-Aspterric Acid, a Carotane-Type Sesquiterpene. II. Synthesis of dl-Aspterric Acid

Total synthesis of dl-aspterric acid (1) has been accomplished.Robinson annulation of the keto ester (2) with methyl vinyl ketone, followed by reduction with LiAlH4 and oxidation with MnO2, afforded the enone alcohol (4), which was converted to the hydroxy-ether (6) via three steps (I2-Ag2O, AgOAc, and alkaline hydrolysis).Successive treatment of 6 with tert-butyldimethylsilyl chloride, tert-BuOK-MeI, NaBH4, Ac2O-pyridine and 5 percent HCl afforded the hydroxy acetate (18).The hydroxy acetate (18) was converted to the hydroxy ketone (20) via catalytic hydrogenation under medium pressure, Jones oxidation, and alkaline hydrolysis.Treatment of 20 with PCl5 gave the norketone (21), which is the degradation product of 1.The dimethylacetal (25) of 20 was treated with Me3SiCN-SnCl2 to give the methoxy cyanides A (26) and B (27).The major methoxy cyanide B (27) was successively treated with KOH, Me3SiCl-NaI, Ac2O, and 5 percent HCl to give the monoacetate (31), which was finally converted to 1 via ring contraction with PCl5 and alkaline hydrolysis. Keywords --- aspterric acid; Robinson annulation; carotane-type sesquiterpene; iodoetherification; ring contraction; C1-unit elongation; ether cleavage

SYNTHESIS OF dl-ASPTERRIC ACID, A CAROTANE TYPE SESQUITERPENE

A carotane type sesquiterpene, aspterric acid (1) was stereoselectively synthesized through Robinson annulation of 2 with MVK, dimethylation of 15, introduction of cyano group to 19 and ring contraction of 25.