87729-38-2Relevant articles and documents
Synthesis of a tripeptide derivative containing the Gln-Arg hydroxyethylene dipeptide isostere
Brewer, Matthias,James, Clint A.,Rich, Daniel H.
, p. 4779 - 4782 (2007/10/03)
(Chemical Equation Presented) The protected hydroxyethylene dipeptide isostere of Gln-Arg and the tripeptide derivative 1 were synthesized as components of potential peptidase inhibitors.
Process for the manufacture of (6E)-leukotriene B4 and intermediates of the said manufacturing process
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, (2008/06/13)
The invention relates to a process for the manufacture of 6-trans-leukotriene B4 (LTB4) of formula STR1 in which a butadienediol is prepared; the hydroxyl groups are esterified to produce a diester and this diester is subjected to a stereospecific reductive elimination using low valency titanium [Ti(0)] to produce a 6-trans triether of formula: STR2 the groups --OA in positions 5 and 12 of which are then converted to --OH groups and the group --CH2 OA in position of which is then converted to a --COOH group, to produce 6-trans-LTB4. The invention also relates to intermediates obtained in the said manufacturing process.
Rotational Selectivity in Cyclobutene Ring Openings. Model Studies Directed toward a Synthesis of Verrucarin A
Trost, Barry M.,McDougal, Patrick G.
, p. 458 - 468 (2007/10/02)
The rotational selectivity in the opening of dissymmetric cyclobutenes to the corresponding dienes is described.In the opening of the monoesters of cis-3,4-cyclobutenedicarboxylic acid, an unusual solvent effect on the ring opening is noted.Switching from Me2SO to 1,2-dichloroethane leads to a 3:1 ratio of the (E,Z)-muconates, favoring the ester on the E double bond.The two isomers can be differentiated by 13C NMR spectroscopy in which the above isomer shows a Δδ for the α,α' carbons of only ca. 2.5 ppm but a Δδ of 5-6 ppm for the isomer having the ester on theZ double bond.Inclusion of the cyclobutene as part of a macrotriolide related to verrucarin A imparts conformational control on the rotational selectivity to favor the E,Z isomer corresponding to the natural products.These relatively simple models inhibit protein synthesis in a fashion reminiscent of the natural products.