- 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
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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.
- Baker, Raymond,Billington, David C.,Ekanayake, Neelakanthie
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- Synthesis and in vivo evaluation of 3,4-disubstituted gababutins
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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.
- 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.
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scheme or table
p. 248 - 251
(2010/04/02)
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- CUPRATE ADDITIONS TO 5-METHOXYCYCLOPENTENONES: A NOVEL STEREOELECTRONIC EFFECT
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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.
- Smith III, Amos B.,Dunlap, Norma K.,Sulikowski, Gary A.
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p. 439 - 442
(2007/10/02)
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