Topic
Ferrier rearrangement
About: Ferrier rearrangement is a research topic. Over the lifetime, 321 publications have been published within this topic receiving 5524 citations.
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75 citations
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TL;DR: A preliminary biological assay revealed that the stereochemistry at the 2-position of lycoricidine plays an important role in its cytotoxic activity.
Abstract: Stereoselective total synthesis of antimitotic alkaloid (+)-lycoricidine (1) and its 2-epimer (30) was accomplished starting from D-glucose. The key steps in this synthesis are (i) a catalytic version of the Ferrier rearrangement for the preparation of the optically active substituted cyclohexenone (the C-ring of lycoricidine) and (ii) a Pd-catalyzed intramolecular Heck-type reaction for construction of the phenanthridone skeleton. A preliminary biological assay revealed that the stereochemistry at the 2-position of lycoricidine plays an important role in its cytotoxic activity
75 citations
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TL;DR: Diastereospecific glycosylation of racemic alcohols by reaction with suitable glycal derivatives in the presence of iodine provides easy access to both enantiomers as illustrated by the preparation of an optically pure α-hydroxy β-lactam that is an intermediate for the semisynthesis of taxol.
Abstract: Diastereospecific glycosylation of racemic alcohols by reaction with suitable glycal derivatives in the presence of iodine provides easy access to both enantiomers as illustrated by the preparation of an optically pure α-hydroxy β-lactam that is an intermediate for the semisynthesis of taxol
73 citations
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TL;DR: 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.
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.
72 citations
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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