Preparation of α-bromoesters via the half esters of malonic acids a novel method for rapid decarboxylation under mild conditions

Synthesis of maculalactone A and derivatives for environmental fate tracking studies

“…The analytical data match those reported in the literature 41. 13 C-NMR (101 MHz, D 2 O): 176.0, 173.3, 139.1, 128.7, 128.6, 126.6, 62.0, 57.3, 35.0, 13.2.…”

“…A published procedure 41 was modified as follows: to a solution of diethyl benzylmalonate (14, 5.11 g, 20.0 mmol, 1.00 eq.) in EtOH (20 ml) a freshly filtered solution of potassium hydroxide (1.39 g, 21.0 mmol, 1.05 eq.)…”

“…The analytical data match those reported in the literature. 41 3-Hydroxy-1,4-diphenylbutan-2-one (16) A published procedure 42 was modified as follows: to a solution of sodium acetate (328 mg, 4.00 mmol, 0.200 eq.) and freshly distilled phenyl acetaldehyde (4.77 ml, 40.0 mmol, 2.00 eq.)…”

“…In order to test this hypothesis, malonate 14 was saponified to the half-ester, 15, in a single step 41 Scheme 3 Synthesis of maculalactone A by a late stage butenolide formation. Synthesis of 15 from 14, as published by Goel et al 41 and converted to the corresponding anhydride with pivaloyl chloride. In the same pot, the anhydride intermediate was reacted with the known α-hydroxy ketone, 16, which itself is accessible via a Benzoin-type Umpolung reaction, 42 to the corresponding keto-diester, 17.…”

Self-immolative linkers for chemical amplification application

“…16 In general, the HVZ reaction requires relatively harsh conditions with temperatures in excess of 100 °C and long reactions times. 17,18 Elimination happens fairly readily following the halogenations, particularly at higher temperatures. 19 That makes this particular technique attractive for highly functionalized aromatic esters synthesis.…”