Total synthesis of secocurvularin, curvulin, and the corresponding carboxylic acids. A convenient application of the enzymatic hydrolysis of acid and base sensitive esters

Natural Product Letters

Volumn 12, Issue 1, 1998, Pages 31-34

  Bracher, Franz ^a,b   Krauss, Jürgen ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

^b UNIVERSITY OF MUNICH   (Germany)

Author keywords

Curvulin; Curvulinic acid; Enzymatic hydrolysis; Esterase; Secocurvularin

Indexed keywords

3,5 DIBENZYLOXYPHENYLACETIC ACID; ACID; BASE; CARBOXYLIC ACID; CURVULIN; ESTER; ESTERASE; PHENYLACETIC ACID DERIVATIVE; POLYKETIDE; SECOCURVULARIN; UNCLASSIFIED DRUG;

ARTICLE; HYDROLYSIS; LIVER; SWINE;

EID: 0031806946     PISSN: 10575634     EISSN: None     Source Type: Journal    
DOI: 10.1080/10575639808048867     Document Type: Article

References (14)

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11. B.W. Bycroft, J.C. Roberts, and P.M. Baker (1964) Studies in mycological chemistry. Part XVI. Synthesis of the di-O-methylcurvularin rearrangement product. J. Chem. Soc., 2289-2292.
12. Typical procedure: To a solution of 150 mg of the ester 5 in acetone (2 ml) and phosphate buffer (pH 6.88; 20 ml) was added hog liver esterase suspension (10 mg/ml; 0.5 ml) and the mixture was stirred at 20°C for 24 h. Extraction with ethyl acetate and evaporation gave analytically pure 7 in 91% yield. Compound 6 was prepared in an analogous manner from 4.
13. +), 195 (42), 167 (100), 151 (42).
14. 5,6b