33404-61-4Relevant academic research and scientific papers
An efficient synthesis of carlosic acid and other 5-carboxymethyltetronates from malates
Schobert, Rainer,Jagusch, Carsten
, p. 2421 - 2425 (2007/10/03)
S-Carlosic acid was prepared in six steps and 32% yield from malic acid. Ring closure was effected by a domino addition-Wittig alkenation reaction with Ph3PCCO. A variant employing resin-bound malates furnished immobilized 5-carboxymethyltetron
PREPARATION OF ACYLTETRONIC ACIDS USING t-BUTYL ACETOTHIOACETATE: TOTAL SYNTHESIS OF THE FUNGAL METABOLITES CAROLIC, CARLOSIC, AND CARLIC ACIDS
Booth, Paul M.,Fox, Christina, M. J.,Ley, Steve V.
, p. 121 - 130 (2007/10/02)
Dianions generated from S-t-butyl acetothioacetate ( 1 ) were alkylated with a variety of electrophiles at the γ-carbon centre.Treatment of the alkylated products with 2-hydroxy esters in the presence of silver(I) salts gave transesterified acetoacetate derivatives in good yields.These acetoacetates were cyclised efficiently to acyltetronic acid derivatives using tetrabutyl ammonium fluoride in THF solution at room temperature.By an appropriate choice of substituents the total synthesis of the fungal metabolite natural products carlosic, carolic, and carlic acids have been achieved.
REGIOSPECIFIC ALKYLATION OF Β-KETOTHIOESTERS AND USE IN THE SYNTHESIS OF ACYL-TETRAONIC ACIDS
Booth, Paul M.,Fox, Christina M. J.,Ley, Steven V.
, p. 5143 - 5146 (2007/10/02)
Anions of t-butylacetothioacetate (1) react with alkylhalides and carbonyl compounds in a regiospecific manner to afford products which are versatile synthetic intermediates as exemplified by short syntheses of the mold metabolites carolic acid (2) and carlosic acid (3).
