115401-40-6Relevant articles and documents
LA REACTION DE WITTIG-HORNER EN MILIEU HETEROGENE IX. BIS ALDOLISATION DES PHOSPHONATES A PARTIR DES DIALDEHYDES ALIPHATIQUES EN MILIEU AQUEUX PEU BASIQUE. SYNTHESE DE CYCLENOLS FONCTIONNELS.
Graff, M.,Dilaimi, A. Al,Seguineau, P.,Rambaud, M.,Villieras, J.
, p. 1577 - 1578 (1986)
Aqueous solutions of glutaraldehyde and succinaldehyde give respectively improved yields of 1-functional 6-cyclohexenols and 5-cyclopentenols, when subjected to WITTIG-HORNER reaction in water at room temperature, with potassium carbonate as a base.
Resolution and utilization of ethyl 5-hydroxycyclopent-1-enecarboxylate: Enantioselective synthesis of (+)-mitsugashiwalactone and (-)-dolichodial
Yamane,Takahashi,Ogasawara
, p. 444 - 448 (1995)
Optically pure ethyl 5-hydroxycyclopent-1-enecarboxylate has been obtained with its acetate in both enantiomeric forms in excellent optical yields from racemic ethyl 5-hydroxycyclopent-1-enecarboxylate by lipase-mediated kinetic resolution. The optically pure (R)-enantiomer thus obtained has been transformed into two naturally occurring iridoid monoterpenes, (+)-mitsugashiwalactone and (-)-dolichodial.
The total synthesis of (-)-7-deoxyloganin via N-heterocyclic carbene catalyzed rearrangement of α,β-unsaturated enol esters
Candish, Lisa,Lupton, David W.
, p. 4836 - 4839 (2010)
The diastereoselective N-heterocyclic carbene (NHC) catalyzed rearrangement of α,β-unsaturated enol ester (S)-2b has been used to assemble dihydropyranone (S)-3b, a material embodying the bicyclic core of the iridoid family of natural products. Elaboration of this intermediate, by chemoselective reduction followed by stereoselective β-glycosylation, has allowed the total synthesis of (-)-7-deoxyloganin (1) to be achieved in four subsequent steps.
Probing the mechanism of allylic substitution of morita-baylis- Hillman acetates (MBHAS) by using the silyl phosphonite paradigm: Scope and applications of a versatile transformation
Kalyva, Maria,Zografos, Alexandros L.,Kapourani, Era,Giambazolias, Evaggelos,Devel, Laurent,Papakyriakou, Athanasios,Dive, Vincent,Lazarou, Yannis G.,Georgiadis, Dimitris
supporting information, p. 3278 - 3289 (2015/03/05)
A P-C bond-forming reaction between silyl phosphonites and Morita-Baylis-Hillman acetates (MBHAs) is explored as a general alternative towards medicinally relevant ?2;-carboxyphosphinic structural motifs. Conversion rates of diversely substituted MBHAs to phosphinic acids 9 or 14that were recorded by using 31P NMR spectroscopy revealed unexpected reactivity differences between ester and nitrile derivatives. These kinetic profiles and DFT calculations support a mechanistic scenario in which observed differences can be explained from the "lateness" of transition states. In addition, we provide experimental evidence suggesting that enolates due to initial P-Michael addition are not formed. Based on the proposed mechanistic scenario in conjunction with DFT calculations, an interpretation of the E/Z stereoselectivity differences between ester and nitriles is proposed. Synthetic opportunities stemming from this transformation are presented, which deal with the preparation of several synthetically capricious phosphinic building blocks, whose access through the classical P-Michael synthetic route is not straightforward.
Concise formal synthesis of (-)-7-deoxyloganin via N-heterocyclic carbene catalysed rearrangement of α,β-unsaturated enol esters
Candish, Lisa,Lupton, David W.
scheme or table, p. 8182 - 8189 (2012/01/04)
NHC catalysed rearrangement of α,β-unsaturated enol esters derived from formyl acetates and cyclopentyl annulated α,β- unsaturated acids provides the cyclopentapyranone core of (-)-7-deoxyloganin (1) with diastereo- and chemoselectivity in 6 steps startin
