123093-92-5Relevant academic research and scientific papers
Synthesis of some highly functionalized thiophene-3-carboxylates and alcohols
Coppola, Gary M.,Damon, Robert E.,Yu, Harvey
, p. 687 - 696 (2007/10/03)
Highly functionalized thiophenes are prepared by two methods. The first uses a lithium-halogen exchange reaction on a trisubstituted 5-bromothiophene 25 to generate the corresponding 5-lithiothiophene 26 which is then reacted with either dimethylformainide or formaldehyde to give the 5-formyl 28 or 5-hydroxymethylthiophene derivative 31 in good yields. These are further transformed to other tetrasubstituted thiophenes. The second method assembles the thiophene ring from three components: a benzyl mercaptan, an aldehyde, and a vinylphosphonate 10. Thus, the benzyl mercaptan is dilithiated then reacted with an appropriate aldehyde to afford a 2-mercapto-2-phenylethanol derivative 37. Michael addition of 37 to 10 followed by oxidation of the hydroxyl group furnishes ketophosphonate 39. An intramolecular Wittig-type reaction produces the thiophene skeleton.
Analogs of mevalonolactone and derivatives thereof
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, (2008/06/13)
Compounds of the formula STR1 in which Y is STR2 X is O or S; Z is --CHOH--CH2 --CHOH--CH2 --COOH, an ester or salt thereof or the lactone thereof; and each of R1, R2 and R3 can be alkyl, cycloalkyl;
