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.
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
