Showing papers on "Ferrier rearrangement published in 1997"
TL;DR: The C3-C14 segment of the novel antitumor agent laulimalide has been constructed enantioselectively by utilizing a catalytic asymmetric hetero Diels-Alder reaction of benzyloxyacetaldehyde and Danishefsky's diene followed by Ferrier rearrangement and asymmetric conjugate reaction as the key steps.
70 citations
TL;DR: Stereospecific glycosylation via the Ferrier rearrangement catalyzed by iodine has been used to obtain both enantiomers of a trans 4-aryl-3-Hydroxy-2-azetidinone and convenient access has become available to all four homochiral stereoisomers of α-hydroxy-β-lactams some of which are synthons for Taxol and analogs.
33 citations
TL;DR: The synthesis of chiral protected 6-deoxy-myo-inositol derivatives from D-galactose is described in this article, where Ferrier rearrangement of hexenogalactopyranosides has been employed to produce the corresponding 6 deoxy-cyclohexanone polyols.
26 citations
TL;DR: In this paper, a Ferrier rearrangement and β-hydroxyketone transposition are key steps in a route to a pancratistatin C-ring precursor.
19 citations
TL;DR: In the course of this study, it was revealed that the Pseudomonas lipase-catalyzed acetylation occurred in a high yield exclusively at the primary alcohols of three Ferrier rearrangement products derived from tri-O-acetyl-D-glucal.
Abstract: N-Acetyl-D-allosamine and its derivatives were synthesized from tri-O-acetyl-D-glucal based on lipase-catalyzed selective protection of primary alcohols, [3,3] sigmatropic rearrangement of allylic trichloroacetimidates, and stereoselective ruthenium-catalyzed dihydroxylation. In the course of this study, it was revealed that the Pseudomonas lipase-catalyzed acetylation occurred in a high yield (> 90%) exclusively at the primary alcohols of three Ferrier rearrangement products derived from tri-O-acetyl-D-glucal.
14 citations
TL;DR: In this article, photoactivatable analogues of 1-l-phosphatidyl-d-myo-inositol 4,5-bisphosphate (PtdIns(4,5)P2 or PtdInsP2) and corresponding 3,4-5-trisphosphates (PndIns(3,4, 5)P3 or PrdInsP3) were prepared from two chiral precursors, methyl α-dglucopyranoside and 1,2-isopropylid
Abstract: Photoactivatable analogues of 1-l-phosphatidyl-d-myo-inositol 4,5-bisphosphate (PtdIns(4,5)P2 or PtdInsP2) and the corresponding 3,4,5-trisphosphate (PtdIns(3,4,5)P3 or PtdInsP3) were prepared from the two chiral precursors, methyl α-d-glucopyranoside and 1,2-isopropylidene-sn-glycerol. Two key synthetic transformations included the Ferrier rearrangement reaction to construct the optically-pure inositol skeleton and the sequential acylation of the primary and secondary hydroxyl groups on the glycerol derivatives. The sn-1-O-(6-aminohexanoyl) PtdInsP2 and PtdInsP3 derivatives were further modified to contain benzophenone photophores in unlabeled and high specific activity tritium-labeled forms.
5 citations
TL;DR: In this article, the C3-C14 segment of the novel antitumor agent laulimalide was constructed enantioselectively by utilizing a catalytic asymmetric hetero Diels-Alder reaction of benzyloxyacetaldehyde and Danishefsky's diene followed by Ferrier rearrangement and asymmetric conjugate reaction as the key steps.
Abstract: The C3-C14 segment of the novel antitumor agent laulimalide has been constructed enantioselectively by utilizing a catalytic asymmetric hetero Diels-Alder reaction of benzyloxyacetaldehyde and Danishefsky's diene followed by Ferrier rearrangement and asymmetric conjugate reaction as the key steps.
1 citations
TL;DR: In this paper, a Ferrier rearrangement and β-hydroxyketone transposition are key steps in a route to a pancratistatin C-ring precursor.
Abstract: A Ferrier rearrangement and β-hydroxyketone transposition are key steps in a route to a pancratistatin C-ring precursor. A key feature of the strategy is the pseudoinversion accomplished by β-hydroxyketone transposition, which allows convenient access from methyl α- d -glucopyranoside. Arylations of the C-ring by intramolecular reductive or non-reductive Pd-catalyzed conjugate addition have been demonstrated, utilizing the C1 hydroxyl to deliver the tethered aryl synthon.