New synthesis of trans,trans-2-[6-(ethoxycarbonyl)hexyl]-3-(ethoxycarbonyl)-4-hydroxycyclopentanone, a useful intermediate for the synthesis of prostaglandins

Abstract

123Registry No. L-Tryptophan ethyl ester p-toluenesulfonate, 71260-63-4; L-tryptophan, 73-22-3; p-toluenesulfonyl chloride, 98-59-9; L-tryptophan benzyl ester hydrochloride, 35858-81-2; glycine ethyl ester hydrochloride, 623-33-6; L-leucine ethyl ester p-toluenesulfonate, 4783-17-9; L-methionine ethyl ester ptoluenesulfonate, 5074-32-8; L-tyrosine ethyl ester p-toluenesulfonate, 5002-67-5; glycine, 56-40-6; L-leucine, 61-90-5; Lmethionine, 63-68-3; L-tyrosine, 60-18-4; glycine benzyl ester p-toluenesulfonate, 1738-76-7; L-leucine benzyl ester p-toluenesulfonate, 1738-77-8; L-tyrosine benzyl ester p-toluenesulfonate,

Substituted thian-4-ones. Part 3. Synthesis and reactions of 2-alkyl-5,6-dihydrothiin-4-ones

“…C,,H,,O,S requires C, 61.00; H, 5.12; S, 13.57%). (23).-A mixture of 2-benzyl-5,6-dihydrothiin-4-one 1,l -dioxide (22) (0.13 g, 0.55 mmol), ethanediol (0.062 g, 1 mmol), and toluene-p-sulphonic acid (5 mg) in benzene (40 ml) was boiled under reflux in a Dean-Stark assembly for 42 h. Additional ethanediol (0.062 mg, 1 mmol) and toluene-p-sulphonic acid (10 mg) were then added and the mixture refluxed for a further 6 h. After the reaction mixture had cooled, anhydrous potassium carbonate (ca. 1 g) was added and the whole stirred for 15 min.…”