19550-72-2Relevant academic research and scientific papers
Stereoselective Total Synthesis of Racemic (3S,4R/3R,4S)- and a Diastereoisomeric Mixture of (6E,10Z)-3,4,7,11-Tetramethyltrideca-6,10-dienal (Faranal); The Trail Pheromone of the Pharaoh's Ant
Baker, Raymond,Billington, David C.,Ekanayake, Neelakanthie
, p. 1387 - 1393 (1983)
Racemic (3S,4R/3R,4S)-faranal has been synthesised by a convergent, stereospecific route which employed the addition of alkylcopper complexes to terminal acetylenes, to generate two trisubstituted double bonds, and a Diels-Alder reaction to establish the relative stereochemistry of the C-3, C-4 methyl groups.A diastereoisomeric mixture of faranals, enriched in the (3S,4S/3R,4R)-enantiomeric pair , has been synthesised by a somewhat shorter route via an intermediate diester, obtained from electrochemical dimerisation of ethyl crotonate.
Synthesis and in vivo evaluation of 3,4-disubstituted gababutins
Blakemore, David C.,Bryans, Justin S.,Carnell, Pauline,Field, Mark J.,Kinsella, Natasha,Kinsora, Jack K.,Meltzer, Leonard T.,Osborne, Simon A.,Thompson, Lisa R.,Williams, Sophie C.
scheme or table, p. 248 - 251 (2010/04/02)
A range of 3,4-alkylated five-membered ring derivatives of gabapentin were synthesised. One compound (21) had an excellent level of potency against α2δ and was profiled in in vivo models of pain and anxiety.
CUPRATE ADDITIONS TO 5-METHOXYCYCLOPENTENONES: A NOVEL STEREOELECTRONIC EFFECT
Smith III, Amos B.,Dunlap, Norma K.,Sulikowski, Gary A.
, p. 439 - 442 (2007/10/02)
Cuprate additions to 5-methoxy-2-cyclopentenone have been found to proceed with moderate to extremely high diastereofacial selectivity, depending upon the specific cuprate and reaction protocol employed.Comparisons with related 5-substitued cyclopentenones suggest that the observed selectivity is not simply steric in nature, but instead reflects a novel stereoelectronic effect.
