54339-95-6Relevant articles and documents
Synthetic research on hepoxilins. 7.* Divergent total synthesis of hepoxilins and related eicosanoids
Mel'nikova,Vasil'eva,Pivnitsky
, p. 1199 - 1208 (1998)
A new synthetic strategy for hydroxy-epoxy eicosanoids formed through the lipoxygenase pathway is developed. It makes use of a single synthon of the central functionalized fragment of the target molecules, namely racemic (E)-CICH2C≡CCHOHCH=CHCH2OBz. Elongation of the carbon chain of the synthon by successive condensations at both ends altenatively with hept-1-yne and hex-5-ynoic acid followed by enantioselective double bond epoxidation and partial hydrogenation of the triple bonds resulted in the syntheses of hepoxilins B3, their potential 8-lipoxygenase analogs, or their enantiomers, depending on the sequence of carbon chain elongations and the chirality of the epoxidation controller used.
Use of hydrolases for the synthesis of cyclic amino acids
Lloyd, Richard C.,Lloyd, Michael C.,Smith, Mark E. B.,Holt, Karen E.,Swift, Jonathan P.,Keene, Philip A.,Taylor, Stephen J. C.,McCague, Raymond
, p. 717 - 728 (2007/10/03)
The synthesis of several cyclic amino acids that have all the necessary structural features to make them ideal scaffolds for use in medicinal chemistry is described. A key step in each synthesis is the use of hydrolase enzymes to define a chiral centre. I
An efficient stereoselective synthesis of Z-(2S)- and Z-(2R)-2-tert-butoxycarbonylamino-6-hydroxyhex-4-enoic acid, key intermediates in the synthesis of (2S,4S,5R)-(-)- and (2R,4R,5S)-(+)-bulgecinine
Holt, Karen E.,Swift, Jonathan P.,Smith, Mark E.B.,Taylor, Stephen J.C.,McCague, Raymond
, p. 1545 - 1548 (2007/10/03)
A concise, scaleable route to both isomers of Z-2-tert-butoxycarbonylamino-6-hydroxyhex-4-enoic acid from 2-butyne-1,4-diol, utilizing L- and D-acylase enzymes is presented. These intermediates were readily converted to multigram quantities of N-Boc-(2S,4
