51731-17-0Relevant articles and documents
An efficient, second-generation synthesis of the signature dioxabicyclo[3.2.1]octane core of (+)-sorangicin a and elaboration of the (Z,Z, E)-triene acid system
Smith III, Amos B.,Dong, Shuzhi
supporting information; experimental part, p. 1099 - 1102 (2009/07/25)
An efficient, second-generation synthesis of the signature dioxabicyclo[3.2.1]octane core of (+)-sorangicin A (1), in conjunction with an effective, stereocontrolled protocol to arrive at the requisite (Z,Z,E)-triene acid system has been developed. Highli
Phorboxazole B synthetic studies: Construction of C(1-32) and C(33-46) subtargets
Paterson, Ian,Steven, Alan,Luckhurst, Chris A.
, p. 3026 - 3038 (2007/10/03)
The convergent syntheses of the C(1-32) and C(33-46) domains of phorboxazole B are described. An iterative cyclocondensation strategy exploited the Jacobsen hetero-Diels-Alder (HDA) reaction as a platform for the synthesis of both the C(5-9) and C(11-15) tetrahydropyran rings. The use of 2-silyloxydiene coupling partners bearing an increasing resemblance to the phorboxazole skeleton was found to lead to a reduction in diastereoselectivity, however, in the case of the C(11-15) ring. The coupling of aldehyde 21 and 2-silyloxydiene 20 by this route provided a C(1-32) fragment which was elaborated to the macrolide core of phorboxazole B. The synthesis of the C(33-46) domain involved a Nozaki-Kishi coupling of aldehyde 31 and vinyl iodide 39. The syntheses of 31 and 39 were highly diastereoselective: an Evans [Cu(Ph-pybox)](SbF6)2-catalysed Mukaiyama aldol reaction formed the cornerstone of the synthesis of 31 whilst a Nagao-Fujita acetate aldol reaction provided a convenient means of installing the sole stereogenic centre of 39.
SYNTHESE DE DERIVES DE L'ACIDE PIPECOLIQUE PAR REACTION D'AZA-DIELS-ALDER : CYCLOADDITIONS ACTIVEES PAR L'IODURE DE ZINC ENTRE LA 1-(PHENYL)-ETHYLIMINE DU GLYOXYLATE DE METHYLE ET LES DIENES RICHES EN ELECTRONS
Abraham, Herve,Theus, Elisabeth,Stella, Lucien
, p. 361 - 366 (2007/10/02)
The methyl N-(1-phenylethyl)-α-iminoacetate undergoes zinc iodide activated aza-Diels-Alder cycloaddition reactions with electron rich conjugated dienes.Cyclic α-amino-acids are formed in good yields, with complete regioselectivity, but the extent of asymmetric induction by the chiral phenethyl group on the nitrogen is low. KEY WORDS: aza-Diels-Alder reactions; heterocyclic α-amino-acids